original_index int64 2 1.77M | extracted_from_file stringclasses 489
values | date_of_experiment timestamp[ns]date | grant_date timestamp[ns]date 1976-01-01 00:01:00 2016-01-01 00:09:00 | is_mapped bool 1
class | rxn_str stringlengths 87 6.12k | reactant_000 stringlengths 1 902 | reactant_001 stringlengths 1 902 ⌀ | reactant_002 null | agent_000 stringlengths 1 540 ⌀ | agent_001 stringlengths 1 852 ⌀ | agent_002 stringlengths 1 247 ⌀ | agent_003 null | agent_004 null | agent_005 null | agent_006 null | agent_007 null | agent_008 null | agent_009 null | agent_010 null | agent_011 null | agent_012 null | agent_013 null | agent_014 null | agent_015 null | agent_016 null | solvent_000 stringclasses 446
values | solvent_001 stringclasses 405
values | solvent_002 null | solvent_003 null | solvent_004 null | solvent_005 null | solvent_006 null | solvent_007 null | solvent_008 null | solvent_009 null | solvent_010 null | temperature float64 -230 30.1k ⌀ | rxn_time float64 0 2.16k ⌀ | procedure_details stringlengths 8 24.5k | product_000 stringlengths 1 484 | product_001 null | yield_000 float64 0 90,205,156,600B ⌀ | yield_001 float64 0 100M ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,083,789 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [Br:1][CH2:2][CH2:3][N:4]([CH2:21][CH2:22][OH:23])[S:5]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[NH:10][C:9]=1[C:18]([NH2:20])=[O:19])(=[O:7])=[O:6].[CH3:24][Si](C=[N+]=[N-])(C)C>ClCCl.CO>[Br:1][CH2:2][CH2:3][N:4]([CH2:21][CH2:22][OH:23])[S:5]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:2... | C[Si](C)(C)C=[N+]=[N-] | NC(=O)c1[nH]c2ccc(O)cc2c1S(=O)(=O)N(CCO)CCBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CO | null | null | null | null | null | null | null | null | null | 25 | 16 | To a solution of 3-{[(2-bromoethyl)(2-hydroxyethyl)amino]sulfonyl}-5-hydroxy-1H-indole-2-carboxamide, described in Step B of Example 51, in 2:1 dichloromethane/MeOH was added excess trimethylsilyldiazomethane (solution in hexane). After stirring at room temperature for 16 hours, the mixture was concentrated in vacuo. P... | COc1ccc2[nH]c(C(N)=O)c(S(=O)(=O)N(CCO)CCBr)c2c1 | null | null | null |
1,556,282 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [F:1][C:2]([C:5]1[CH:9]=[C:8]([NH:10][C:11](=[O:19])OC2C=CC=CC=2)[O:7][N:6]=1)([CH3:4])[CH3:3].[NH2:20][C:21]1[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=1.CN(C1C=CC=CN=1)C>C1COCC1>[F:1][C:2]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=2)=[O:19])[O:7][N:6]=1)([CH3:3])[... | CC(C)(F)c1cc(NC(=O)Oc2ccccc2)on1 | Nc1cccc(O)c1 | null | CN(C)c1ccccn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To THF (10 mL) was added phenyl 3-(2-fluoropropan-2-yl)isoxazol-5-ylcarbamate from the previous step (500 mg, 1.9 mmol), 3-aminophenol (207 mg, 1.9 mmol) and dimethylaminopyridine (60 mg, 0.5 mmol) and the mixture stirred overnight at room temperature. The mixture was concentrated in vacuo and purified by chromatograph... | CC(C)(F)c1cc(NC(=O)Nc2cccc(O)c2)on1 | null | 74 | null |
656,612 | ord_dataset-f5d908a6dcb44353a706166b5e9f7f88 | null | 2004-01-01T00:12:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C@@H:16]1([NH2:26])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18][CH2:17]1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][NH:26][C@@H:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:2... | N[C@H]1CCCc2ccccc21 | O=Cc1ccc(-c2ccc(F)cc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 4′-Fluoro[1,1′-biphenyl]-4-carbaldehyde and (1S)-1,2,3,4-tetrahydro-1-naphthalenylamine were processed as described in Example 1A to provide the title compound. | Fc1ccc(-c2ccc(CN[C@H]3CCCc4ccccc43)cc2)cc1 | null | null | null |
1,675,622 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([OH:12])=[O:11].I[CH3:14]>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:14])[C:10]([OH:12])=[O:11] | CI | O=C(O)Cc1ccc(Cl)cc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | prepared from 2,4-dichlorophenylacetic acid and iodomethane; | CC(C(=O)O)c1ccc(Cl)cc1Cl | null | null | null |
979,318 | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | null | 2010-01-01T00:07:00 | true | [CH:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[CH3:11])([CH3:3])[CH3:2].Br[CH2:13][C:14]([O:16][CH3:17])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:6][C:5]=1[CH3:11])([CH3:3])[CH3:2] | Cc1cc(O)ccc1C(C)C | COC(=O)CBr | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 4-isopropyl-3-methylphenol (10.0 g, 67 mmol), methyl bromoacetate (6.6 mL, 70 mmol) and anhydrous potassium carbonate (10.1 g, 73 mmol) in 2-butanone (100 mL) was heated to reflux for 20 h. The mixture was cooled and partitioned between water (350 mL) and ethyl acetate (100 mL). The organic phase was wash... | COC(=O)COc1ccc(C(C)C)c(C)c1 | null | null | null |
192,955 | ord_dataset-11b3c3b41eda49e196ec983a65d3b2c0 | null | 1989-01-01T00:07:00 | true | [CH3:1][N:2]1[C@H:16]2[C@@H:6]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[C:13]([C:18]#[C:19][CH2:20][O:21]C2CCCCO2)[NH:12]4)[CH2:5][C@H:4]([NH:28][C:29](=[O:35])[N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])[CH2:3]1.O.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[OH:21][C:20]#[C:19][CH2:18][C:13]1[... | CCN(CC)C(=O)N[C@H]1C[C@@H]2c3cccc4[nH]c(C#CCOC5CCCCO5)c(c34)C[C@H]2N(C)C1 | null | null | Cc1ccc(S(=O)(=O)[O-])cc1 | c1cc[nH+]cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | null | null | 213 mg (0.45 mmol) of 3-[6-methyl-2-[3-(tetrahydropyran-2-yloxy)propynyl]-8α-ergolinyl]-1,1-diethylurea is heated under reflux in 10 ml of ethanol with 2 ml of water and 176 mg (0.7 mmol) of pyridinium p-toluenesulfonate under argon for one hour. After evaporation and distribution in ethyl acetate and saturated bicarbo... | CCN(CC)C(=O)N[C@H]1C[C@@H]2c3cccc4[nH]c(CC#CO)c(c34)C[C@H]2N(C)C1 | null | 50.7 | null |
1,611,316 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [CH3:1]OC([C@@H]1C[C@@H](O)CCN1C(OC(C)(C)C)=O)=O.[CH3:19][O:20][C:21]([C@@H:23]1[CH2:27][C@H:26]([NH2:28])[CH2:25][N:24]1[CH2:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)=[O:22]>>[CH3:19][O:20][C:21]([C@@H:23]1[CH2:27][C@H:26]([NH2:28])[CH2:25][CH2:1][N:24]1[CH2:29][CH:30]1[CH2:31][CH2:32][CH2:33][CH2:34][CH2:... | COC(=O)[C@@H]1C[C@H](N)CN1CC1CCCCC1 | COC(=O)[C@@H]1C[C@@H](O)CCN1C(=O)OC(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | (2S,4R)-4-amino-1-cyclohexylmethyl-piperidine-2-carboxylic acid methyl ester was prepared from (2S,4S)-4-hydroxy-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester in a similar reaction sequence used in the preparation of (2S,4S)-4-amino-1-cyclohexylmethyl-pyrrolidine-2-carboxylic acid methyl ester. MS ... | COC(=O)[C@@H]1C[C@H](N)CCN1CC1CCCCC1 | null | null | null |
1,016,745 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C1(S([N:18]2[C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[C:20]([C:27]3[CH:32]=[CH:31][N:30]=[C:29](Cl)[N:28]=3)=[CH:19]2)(=O)=O)C=CC=CC=1>>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:29]2[N:28]=[C:27]([C:20]3[C:21]4[C:22](=[N:23][CH:24]=[CH:25][CH:26]=4)[NH:18][CH:19]=... | O=S(=O)(c1ccccc1)n1cc(-c2ccnc(Cl)n2)c2cccnc21 | Nc1ccc(O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using the procedure of example 1, 4-aminophenol (177 mg) was reacted with compound 1f (200 mg) to provide compound 39 (48 mg, 29%). 1H NMR (400 MHz, CD3OD) δ 8.48 (d, J=8.0 Hz, 1H), 8.24 (s, 1H), 8.23 (d, J=8.0 Hz, 1H), 8.12 (d, J=4.8 Hz, 1H), 7.45 (d, J=8.0 Hz, 1H), 7.05 (dd, J=8.0 Hz, 5.6 Hz, 1H), 7.00 (d, J=5.2 Hz, ... | Oc1ccc(Nc2nccc(-c3c[nH]c4ncccc34)n2)cc1 | null | 29.3 | null |
61,831 | ord_dataset-d9fb402fe3e745c1893a29161cc5dda2 | null | 1980-01-01T00:01:00 | true | [NH:1]1[C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][C:4]=2[N:3]=[C:2]1[SH:14])[CH:11]=[CH:10][CH:9]=[CH:8]3.[ClH:15].[Cl:16][CH2:17][C:18]1[NH:19][CH2:20][CH2:21][N:22]=1>CN(C)C=O.C1(C)C=CC=CC=1>[ClH:16].[ClH:15].[NH:22]1[CH2:21][CH2:20][N:19]=[C:18]1[CH2:17][S:14][C:2]1[NH:3][C:4]2[CH:13]=[C:12]3[C:7](=[CH:6][C:5]=2[N:1]=1)[CH:... | Sc1nc2cc3ccccc3cc2[nH]1 | ClCC1=NCCN1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | null | 10.0 g of 1H-Naphth[2,3-d]imidazole-2-thiol and 8.0 g of 2-chloromethylimidazoline-hydrochloride were heated for 3 hours at 90° in 50 ml of dimethylformamide. The reaction mixture was cooled to room temperature and then diluted with 200 ml of toluene. The residue was suctioned filtered, washed well with toluene, and cr... | c1ccc2cc3[nH]c(SCC4=NCCN4)nc3cc2c1 | null | 58.1 | null |
1,607,501 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | Br[C:2]1[C:3]([O:8][CH2:9][CH2:10][OH:11])=[N:4][CH:5]=[CH:6][CH:7]=1.[F:12][C:13]1[CH:18]=[C:17](B2OC(C)(C)C(C)(C)O2)[CH:16]=[CH:15][C:14]=1[C:28]1[CH:29]=[N:30][C:31]([NH2:34])=[N:32][CH:33]=1>>[NH2:34][C:31]1[N:32]=[CH:33][C:28]([C:14]2[CH:15]=[CH:16][C:17]([C:2]3[C:3]([O:8][CH2:9][CH2:10][OH:11])=[N:4][CH:5]=[CH:6]... | OCCOc1ncccc1Br | CC1(C)OB(c2ccc(-c3cnc(N)nc3)c(F)c2)OC1(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared in a manner similar to that described in Example 88 using 2-((3-bromopyridin-2-yl)oxy)ethanol and 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine. MS (ESI): mass calcd. for C17H15FN4O2, 326.12; m/z found, 326.9 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 8.47 ... | Nc1ncc(-c2ccc(-c3cccnc3OCCO)cc2F)cn1 | null | null | null |
574,337 | ord_dataset-f4512fe8cd804ac79da66cbc0c2b9d42 | null | 2002-01-01T00:12:00 | true | [OH:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][C@@H:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:9]3[CH:18]=[CH:19][CH:20]=[CH:21][C:8]=3[CH2:7][C:6]=2[CH:22]=1.[N:23]1[C:32]2[NH:31][CH2:30][CH2:29][CH2:28][C:27]=2[CH:26]=[CH:25][C:24]=1[CH2:33][CH2:34]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)... | OCCc1ccc2c(n1)NCCC2 | CCOC(=O)C[C@@H]1Cc2ccc(O)cc2Cc2ccccc21 | null | CC(C)OC(=O)N=NC(=O)OC(C)C | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 18 | To a solution of ethyl (S)-10,11 -dihydro-3-hydroxy-5H-dibenzo[a,d]cycloheptene-10-acetate (200 mg, 0.67 mmole), 2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)-1 -ethanol (241 mg, 1.35 mmole), and PPh3 (354 mg, 1.35 mmole) in dry THF (5 mL) was added diisopropyl azodicarboxylate (0.27 mL, 1.35 mmole) at 0° C. The mixture... | CCOC(=O)C[C@@H]1Cc2ccc(OCCc3ccc4c(n3)NCCC4)cc2Cc2ccccc21 | null | 30.7 | null |
92,562 | ord_dataset-dba7c8cf38834984ba5e6376158f46fe | null | 1982-01-01T00:03:00 | true | [Se](=O)=[O:2].[CH3:4][O:5][C:6]1[CH:7]=[C:8]([C:14]2[C:20]3[CH:21]=[C:22]([O:27][CH3:28])[C:23]([O:25][CH3:26])=[CH:24][C:19]=3[CH:18]([CH2:29][CH3:30])[C:17]([CH3:31])=[N:16][N:15]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH3:13]>O1CCOCC1>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([C:14]2[C:20]3[CH:21]=[C:22]([O:27][CH3:28])[C:23]([O:25][... | CCC1C(C)=NN=C(c2ccc(OC)c(OC)c2)c2cc(OC)c(OC)cc21 | O=[Se]=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | 6.05 g of selenium dioxide are added within 1.5 hours to a stirred suspension of 19.1 g (0.05 mole) of 1-(3,4-dimethoxyphenyl)-4-methyl-5-ethyl-7,8-dimethoxy-5H-2,3-benzodiazepine in 150 ml of 80% aqueous dioxane at an inner temperature of 84° to 87° C. The metallic selenium is removed from the mixture by clarification... | CCC1C(C=O)=NN=C(c2ccc(OC)c(OC)c2)c2cc(OC)c(OC)cc21 | null | 97.4 | null |
1,604,416 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][O:14][C:15]1[N:20]=[CH:19][C:18]([C:21]([NH:23][CH:24]2[CH2:29][CH2:28][CH2:27][N:26]([CH2:30][C:31]([OH:33])=O)[CH2:25]2)=[O:22])=[CH:17][CH:16]=1.[F:34][C:35]([F:39])([F:38])[CH2:36][NH2:37]>>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2... | Cc1onc(-c2ccccc2)c1COc1ccc(C(=O)NC2CCCN(CC(=O)O)C2)cn1 | NCC(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | As described for example 42, (3-{[6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine-3-carbonyl]-amino}-piperidin-1-yl)-acetic acid (70 mg, 0.16 mmol) was converted, using 2,2,2-trifluoroethylamine instead of methylamine, to the title compound (51 mg, 62%) which was obtained as an off white solid. MS: m/e=532.0 [M+H]+... | Cc1onc(-c2ccccc2)c1COc1ccc(C(=O)NC2CCCN(CC(=O)NCC(F)(F)F)C2)cn1 | null | 62 | null |
271,898 | ord_dataset-347c0709d28a44dea43ca42052be4db3 | null | 1993-01-01T00:07:00 | true | O1CCCC1.[CH2:6]([NH:13][C:14](=O)[C:15]1[C:16](=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:17]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=O)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].Cl>CO>[CH2:20]([NH:19][CH2:17][C:16]1[C:15]([CH2:14][NH:13][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:30]... | CCCCCCCNC(=O)c1ccccc1C(=O)NCCCCCCC | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | null | null | To a 1M solution of borane-tetrahydrofuran complex (24 ml) was added dropwise under ice cooling a 5 ml tetrahydrofuran solution containing 3.6 g of N,N'-diheptylphthalamide obtained in Example 2 under an argon gas stream, and the mixture was warmed up slowly and then heated under reflux for one hour. After cooling, 2 m... | CCCCCCCNCc1ccccc1CNCCCCCCC | null | 12.9 | null |
759,380 | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | null | 2007-01-01T00:03:00 | true | [CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][C:14](=[O:18])[NH:15]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][C:14](=[O:18])[N:15]2[CH3:19])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1 | O=C1Cc2ccc(OCc3ccccc3)cc2N1 | O=C([O-])[O-] | null | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | CI | null | null | null | null | null | null | null | null | null | null | null | A mixture of 6-benzyloxy-1,3-dihydro-2H-indol-2-one (Example 9) (0.12 g; 0.5 mmol), K2CO3 (0.07 g; 0.5 mmol) and CH3I (0.031 ml) in acetone (5 ml) was refluxed under argon atmosphere for 6 hours. After evaporation to dryness, the residue was purified by flash chromatography eluting with petroleum ether/AcOEt 60/40 to g... | CN1C(=O)Cc2ccc(OCc3ccccc3)cc21 | null | 31 | null |
755,057 | ord_dataset-1b0cd79134f0450eaac8396a4f956c30 | null | 2007-01-01T00:02:00 | true | Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([N+:11]([O-:13])=[O:12])=[CH:4][N:3]=1.[NH:14]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>C1COCC1>[N:14]1([C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([N+:11]([O-:13])=[O:12])=[CH:4][N:3]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1 | C1CCCNCC1 | O=[N+]([O-])c1cnc(Cl)c([N+](=O)[O-])c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 60 | null | 3 g (14.7 mmol) of 2-chloro-3,5-dinitropyridine, 10 ml of THF and 30 mmol of azepane were placed in a round-bottomed flask. The mixture was maintained at 60° C. for 15 hours with stirring and was then poured into an ice-water mixture with stirring. The precipitate formed was filtered off by suction and dried under vacu... | O=[N+]([O-])c1cnc(N2CCCCCC2)c([N+](=O)[O-])c1 | null | 41.9 | null |
1,400,060 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][NH2:9])=[N:6][CH:7]=1.[CH:10](O)=[O:11].[OH-].[NH4+]>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][NH:9][CH:10]=[O:11])=[N:6][CH:7]=1 | O=CO | NCc1ccc(F)cn1 | null | [NH4+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | null | In a round-bottomed flask, (5-fluoro-pyridin-2-yl)methylamine (557 mg, 4.42 mmol) was dissolved in 88% formic acid (3.6 ml, 82.6 mmol). The brown solution was stirred at reflux in an oil bath overnight. The reaction mixture was cooled to 0° C. and adjusted carefully to pH=9 by addition of 25% aqueous ammonium hydroxide... | O=CNCc1ccc(F)cn1 | null | 90.1 | null |
1,513,759 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8](OCC)=[O:9])=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([CH:21]([CH3:23])[CH3:22])[N:15]=2)[CH:3]=1.[NH3:24].CO>>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([NH2:24])=[O:9])=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([CH:21]([CH3:23])[CH3:22])[N:15]=2)[CH:3]=1 | CCOC(=O)c1nnc(Cl)cc1Nc1ccc(F)c(C(C)C)n1 | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 40 | 18 | To a solution of ethyl 6-chloro-4-(5-fluoro-6-isopropylpyridin-2-ylamino)pyridazine-3-carboxylate (290 mg, 856 μmol) was added 7N ammonia in MeOH (12.2 mL, 85.6 mmol). The mixture was stirred at 40° C. for 18 h, after which the solvent was removed to give 6-chloro-4-(5-fluoro-6-isopropylpyridin-2-ylamino)pyridazine-3-c... | CC(C)c1nc(Nc2cc(Cl)nnc2C(N)=O)ccc1F | null | 94 | null |
700,045 | ord_dataset-bbd7e53f000345838ad4920a07a169ff | null | 2006-01-01T00:03:00 | true | [CH3:1][NH:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]#[C:10][CH2:11][OH:12])[CH2:5][CH2:4]1.Br[C:14]1[N:19]=[CH:18][C:17]([Br:20])=[CH:16][N:15]=1.C(N(C(C)C)C(C)C)C>>[Br:20][C:17]1[CH:16]=[N:15][C:14]([N:2]([CH3:1])[C@H:3]2[CH2:4][CH2:5][C@H:6]([C:9]#[C:10][CH2:11][OH:12])[CH2:7][CH2:8]2)=[N:19][CH:18]=1 | Brc1cnc(Br)nc1 | CN[C@H]1CC[C@H](C#CCO)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | 80 | null | A mixture of 0.51 g (3.05 mmol) trans-3-(4-Methylamino-cyclohexyl)-prop-2-yn-1-ol, 0.87 g (3.66 mmol) 2,5-dibromo-pyrimidine [Brown, Desmond J.; Arantz, B. W., Pyrimidine reactions. XXII. Relative reactivities of corresponding chloro-, bromo-, and iodopyrimidines in aminolysis. J. Chem. Soc. C (1971), Issue 10, 1889–91... | CN(c1ncc(Br)cn1)[C@H]1CC[C@H](C#CCO)CC1 | null | null | null |
217,298 | ord_dataset-67ed03c283094854909157b1038e38e3 | null | 1990-01-01T00:10:00 | true | [Si:1]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[O:15])[C@H:11]([CH2:27]OS(C)(=O)=O)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:33]([O-:36])(=[S:35])[CH3:34].[K+]>CN(C)C=O>[C:33]([S:35][CH2:27][C@@H:11]1[CH2:10][C@@H:9]([O... | CC([O-])=S | CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@H](COS(C)(=O)=O)N(C(=O)OCc2ccc([N+](=O)[O-])cc2)C1 | null | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 0 | 1 | To a solution of (2S,4R)-4-t-butyldimethylsilyloxy-2-methanesulfonyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (5.21 g) in N,N-dimethylformamide (52 ml) was added potassium thioacetate (1.83 g) and the mixture was stirred at 50°-60° C. for 1 hour. The reaction mixture was poured into ice-water (150 ml) and extra... | CC(=O)SC[C@@H]1C[C@@H](O[Si](C)(C)C(C)(C)C)CN1C(=O)OCc1ccc([N+](=O)[O-])cc1 | null | 94.1 | null |
245,308 | ord_dataset-5eb2900a93c842ee98f26c305e657b61 | null | 1992-01-01T00:04:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(OCC)=O.[CH3:23][NH2:24].[Cl-].[Na+]>O1CCCC1.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14](=[O:16])[NH:24][CH3:23])=[O:7])([CH3:4])([CH3:3])[CH3:2] | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(=O)O | CN | null | CCOC(=O)Cl | [Cl-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 1 | 9.91 ml of triethylamine were added at -40° C. to a solution of 15.03 g of (2S, 4R)-1-(t-butoxycarbonyl)-4-hydroxy-2-pyrrolidinecarboxylic acid dissolved in 250 ml of dry tetrahydrofuran, and then a solution of 6.81 ml of ethyl chloroformate in 30 ml of dry tetrahydrofuran was added at -30° to -40° C. to the resulting ... | CNC(=O)[C@@H]1C[C@@H](O)CN1C(=O)OC(C)(C)C | null | null | null |
1,621,157 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | Cl.[NH2:2][C@@H:3]1[CH2:7][CH2:6][N:5]([CH2:8][C@@H:9]([C:11]2[CH:20]=[CH:19][C:14]3[C:15](=[O:18])[O:16][CH2:17][C:13]=3[C:12]=2[CH3:21])[OH:10])[CH2:4]1.[C:22]([C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1)#[N:23]>>[C:22]([C:24]1[CH:25]=[CH:26][C:27]([S:30]([NH:2][C@@H:3]2[CH2:7][CH2:6][N:... | Cc1c([C@@H](O)CN2CC[C@@H](N)C2)ccc2c1COC2=O | N#Cc1ccc(S(=O)(=O)Cl)cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 4-Cyano-N—((R)-1-((R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)pyrrolidin-3-yl)benzenesulfonamide was prepared in a similar fashion to that described for the synthesis of EXAMPLE 14 starting from 5-{(1R)-2-[(3R)-3-Aminopyrrolidin-1-yl]-1-hydroxyethyl}-4-methyl-2-benzofuran-1(3H)-one hydrochloride... | Cc1c([C@@H](O)CN2CC[C@@H](NS(=O)(=O)c3ccc(C#N)cc3)C2)ccc2c1COC2=O | null | null | null |
448,971 | ord_dataset-a4f0b79f6b9847168861270b79f84afa | null | 1999-01-01T00:11:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[H-].[Na+].Cl.[N:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22]Cl)[CH:17]=1.O>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:22][C:18]1[CH:17]=[N:16][CH:21]=[CH:20][CH:19]=1)[CH:8]=[CH:7]2)([O-:3])=[O:2] | ClCc1cccnc1 | O=[N+]([O-])c1ccc2[nH]ccc2c1 | null | Cl | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | 25 | 0.25 | 5-Nitroindole (0.49, 3 mmol) was treated with sodium hydride (0.198 g, 6.6 mmol) in dry dimethylformamide (20 ml). After 15 min at room temperature, 3-picolyl chloride hydrochloride (0.49 g, 3 mmol) was added and the mixture was stirred at room temperature for 24 h, then poured into water. The precipitate was filtered ... | O=[N+]([O-])c1ccc2c(ccn2Cc2cccnc2)c1 | null | 88.2 | null |
52,676 | ord_dataset-3d470a6df4a04b1996e024a38c53e818 | null | 1979-01-01T00:03:00 | true | C(O[C:4]([C:6]1[O:7][C:8]([SH:11])=[N:9][N:10]=1)=[O:5])C.[CH2:12]([NH2:14])[CH3:13]>>[CH2:12]([NH:14][C:4]([C:6]1[O:7][C:8]([SH:11])=[N:9][N:10]=1)=[O:5])[CH3:13] | CCN | CCOC(=O)c1nnc(S)o1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This product (m.p. 210° C. with decomp.) was prepared by reacting 2-ethoxycarbonyl-1,3,4-oxadiazole-5-thiol with ethylamine in a manner similar to that described in the procedure of Example XVI, Part C as hereinafter set forth. | CCNC(=O)c1nnc(S)o1 | null | null | null |
841,700 | ord_dataset-074f86301ec5441ab3b52d902ac06949 | null | 2008-01-01T00:09:00 | true | [N:1]1([CH2:6][CH2:7][S:8]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[O:9])[CH:5]=[CH:4][N:3]=[N:2]1.[H-].[Na+].Cl[CH2:21][C:22]1[C:23]([CH3:38])=[N:24][C:25]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=2)=[CH:26][CH:27]=1.O>CN(C)C=O>[CH3:38][C:23]1[C:22]([CH2:21][O:1... | Cc1nc(-c2ccc(C(F)(F)F)cc2)ccc1CCl | O=S(CCn1ccnn1)Cc1ccc(O)cc1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 0 | 0.5 | A solution of 126 mg (mmol) 4-(2-[1,2,3]triazol-1-yl-ethanesulfinylmethyl)-phenol in 4.0 ml N,N-dimethylformamide was treated at 0° C. with 14 mg (0.55 mmol) of 95% sodium hydride and stirred at 0° C. for 30 min., then 143 mg (0.50 mmol) 3-chloromethyl-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine were added and stirr... | Cc1nc(-c2ccc(C(F)(F)F)cc2)ccc1COc1ccc(CS(=O)CCn2ccnn2)cc1 | null | 51.9 | null |
1,620,523 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][OH:10].[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]=[CH2:19])=[CH:14][CH:13]=1.CCN(CC)CC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C=O)C>[F:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:9][OH:10])=[C:2](/[CH:19]=[CH:18]/[C:15]2... | OCc1ccc(F)cc1Br | C=Cc1ccc(F)cc1 | null | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 150 | null | Charged (2-bromo-4-fluorophenyl)methanol (954 mg, 4.65 mmol), 4-fluoro-1-vinylbenzene (1.14 g, 9.31 mmol), Pd(PPh3)2Cl2 (49 mg, 0.07 mmol), Et3N (942 mg, 9.31 mmol) and DMF (5 mL) to a sealed tube, the mixture was then purged with nitrogen, heated to 150° C. for 3 h in microwave oven. The reaction mixture was filtered,... | OCc1ccc(F)cc1/C=C/c1ccc(F)cc1 | null | 49.7 | null |
923,473 | ord_dataset-cc0899cd744f4f7f8e7f2463560faad1 | null | 2009-01-01T00:12:00 | true | [NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15](Cl)(=[O:17])=[O:16]>>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([NH:1][C@@H:2]([CH2:3][OH:4])[C:5]([OH:7])=[O:6])(=[O:17])=[O:16] | O=S(=O)(Cl)c1ccccc1Cl | N[C@@H](CO)C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In analogy to example 2, L-serine was reacted with 2-chlorobenzenesulfonyl chloride to give (S)-2-(2-chloro-benzenesulfonylamino)-3-hydroxy-propionic acid as a colorless solid. MS: 278.1 ([M−H]−) | O=C(O)[C@H](CO)NS(=O)(=O)c1ccccc1Cl | null | null | null |
1,667,481 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([OH:9])[N:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]=[C:19]=[O:20]>CN(C=O)C>[F:8][C:7]1[C:2]([NH:1][C:19]([NH:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[O:11][CH3:10])=[O:20])=[N:3][C:4]([OH:9])=[N:5][CH:6]=1 | Nc1nc(O)ncc1F | COc1ccccc1N=C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 1 | To a magnetically stirred mixture of 4-amino-2-hydroxy-5-fluoropyrimidine (150 mg, 1.16 mmol) in dry DMF (3.5 mL) was added 2-methoxyphenyl isocyanate (170 μL, 1.28 mmol) and the white suspension was allowed to stir at room temperature for 60 min. The mixture was heated to 55° C. for 3 h, and then allowed to stir at ro... | COc1ccccc1NC(=O)Nc1nc(O)ncc1F | null | 83.3 | null |
379,733 | ord_dataset-993feac5ecf54388aa6326a220e46db3 | null | 1997-01-01T00:10:00 | true | Cl[C:2]([O:4][CH2:5][CH2:6][Cl:7])=[O:3].[CH2:8]([OH:10])[CH3:9].N1C=CC=CC=1>C(Cl)Cl>[C:2](=[O:3])([O:4][CH2:5][CH2:6][Cl:7])[O:10][CH2:8][CH3:9] | O=C(Cl)OCCCl | CCO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 0.17 | To a solution of chloroethyl chloroformate (23.16 g, 0.162 mol) and ethanol (7.45 g, 0.162 mol) in methylene chloride (200 ml), pyridine (12.82 g, 0.162 mol) was added at 0° C. After 10 min at 0° C. and 21 hours at 25° C. the reaction mixture was washed with aqueous hydrochloric acid (100 ml), aqueous saturated sodium ... | CCOC(=O)OCCCl | null | 74.8 | null |
578,439 | ord_dataset-a9ba4801408c4b01922886164c10a391 | null | 2003-01-01T00:01:00 | true | [CH2:1]([O:8][C:9](=[O:42])[C@@H:10]([NH:22][C:23](=[O:41])[C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH2:35][CH2:34][CH:33]([CH:36](OC)[O:37]C)[CH2:32][CH2:31]2)=[CH:26][CH:25]=1)[CH2:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)C... | COC(OC)C1CCN(c2ccc(C(=O)N[C@@H](CC(=O)OCc3ccccc3)C(=O)OCc3ccccc3)cc2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 1 | A solution of (2S)-2-{[4-(4-(dimethoxymethyl)piperidin-1-yl)benzoyl]-amino}-butanedioic acid dibenzyl ester (0.21 g, 0.4 mmol) in methylene chloride (10 mL) containing trifluoroacetic acid (0.2 ml, 2.6 mmol) was stirred at ambient temperature for 1 hour. The reaction was concentrated in vacuo to give the product which ... | O=CC1CCN(c2ccc(C(=O)N[C@@H](CC(=O)OCc3ccccc3)C(=O)OCc3ccccc3)cc2)CC1 | null | null | null |
978,625 | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | null | 2010-01-01T00:07:00 | true | [CH:1]1([NH:4][C:5](=[O:30])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19]([C:23]3[CH2:24][CH2:25][N:26]([CH3:29])[CH2:27][CH:28]=3)=[N:18][N:17]=[CH:16]4)[CH:7]=2)[CH2:3][CH2:2]1.[H][H]>[Pd].C(OCC)(=O)C>[CH:1]1([NH:4][C:5](=[O:30])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[... | Cc1ccc(C(=O)NC2CC2)cc1-c1ccc2c(C3=CCN(C)CC3)nncc2c1 | [H][H] | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of N-cyclopropyl-4-methyl-3-(1-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)phthalazin-6-yl)benzamide (20 mg, 50 μmol), 20 mg 10% palladium on activated carbon in 20 mL ethyl acetate was stirred under 50 psi hydrogen at 22° C. After 2 h reaction, the reaction was monitored for product (MS=401) and starting materi... | Cc1ccc(C(=O)NC2CC2)cc1-c1ccc2c(C3CCN(C)CC3)nncc2c1 | null | 49.9 | null |
1,038,679 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:18])=[C:6]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][N:9]=2)[CH:7]=1.[OH-].[Li+]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:18])=[C:6]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][N:9]=2)[CH:7]=1 | COC(=O)c1ccc(-c2cc(F)ccc2O)nc1 | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 0 | 0.5 | methyl 6-(5-fluoro-2-hydroxyphenyl)nicotinate (1.47 g, 6.0 mmol) was dissolved in MeOH (35 ml) and cooled to 0° C. Lithium hydroxide (0.71 g, 30.0 mmol) was then added and the mixture stirred at 0° C. for 0.5 h. The mixture was then allowed to warm to room temperature. Additional lithium hydroxide (0.43 g, 18.0 mmol) w... | O=C(O)c1ccc(-c2cc(F)ccc2O)nc1 | null | 82.2 | null |
1,611,125 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [Cl:1][C:2]1[C:3]([CH:16]2[O:24][C:17]2([CH3:23])[C:18]([O:20]CC)=[O:19])=[C:4]([O:14][CH3:15])[C:5]2[C:10]([C:11]=1[O:12][CH3:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.[OH-].[K+]>CCO>[Cl:1][C:2]1[C:3]([CH:16]2[O:24][C:17]2([CH3:23])[C:18]([OH:20])=[O:19])=[C:4]([O:14][CH3:15])[C:5]2[C:10]([C:11]=1[O:12][CH3:13])=[CH:9][CH:8]=[... | CCOC(=O)C1(C)OC1c1c(Cl)c(OC)c2ccccc2c1OC | null | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | 0.5 | Darzens esters 70 (0.193 g, 0.550 mmol) were dissolved in EtOH (10.0 mL) and then KOH (0.200 g, 3.56 mmol) was added to the reaction. The reaction was heated to boiling and stirred at this temperature for 30 minutes. The reaction was then cooled, acidified, and extracted with ethyl acetate. The organic layer was washed... | COc1c(Cl)c(C2OC2(C)C(=O)O)c(OC)c2ccccc12 | null | 100.9 | null |
1,379,161 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [CH2:1]([O:3][P:4]([CH:9]([P:28]([O:33][CH2:34][CH3:35])([O:30][CH2:31][CH3:32])=[O:29])[CH2:10][C:11]1[N:15]2[CH:16]=[CH:17][CH:18]=[C:19]([O:20]CC3C=CC=CC=3)[C:14]2=[N:13][CH:12]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]>C(O)C>[CH2:34]([O:33][P:28]([CH:9]([P:4]([O:3][CH2:1][CH3:2])([O:5][CH2:6][CH3:7])=[O:8])[CH2:10][C:1... | CCOP(=O)(OCC)C(Cc1cnc2c(OCc3ccccc3)cccn12)P(=O)(OCC)OCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | 12 | As shown in FIG. 7, [2-(8-Benzyloxy-imidazo[1,2-α]pyridin-3-yl)-1-(diethoxy-phosphoryl)-ethyl]-phosphonic acid diethyl ester 35 (Example 21) (1.5 g, 2.86 mmol) and ethanol (30 mL) were mixed in a 250-mL round bottomed flask and purged with nitrogen for 5 minutes. Palladium on carbon (10%, 50% wet, 1.5 g) was then added... | CCOP(=O)(OCC)C(Cc1cnc2c(O)cccn12)P(=O)(OCC)OCC | null | 72 | null |
723,836 | ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | null | 2006-01-01T00:08:00 | true | Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[C:7]([NH2:12])[C:6]3[N:13]=[C:14]([CH2:20][CH3:21])[N:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:5]=3[C:4]=2[CH:3]=1.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24](B(O)O)[CH:23]=1>>[CH2:20]([C:14]1[N:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:5]2[C:4]3[CH:3]=[C:2]([C:24]4[CH:23]=[N:22][CH:27]=[CH:... | OB(O)c1cccnc1 | CCc1nc2c(N)nc3ccc(Br)cc3c2n1CC(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 8-Bromo-2-ethyl-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine and pyridine-3-boronic acid were coupled according to the general procedure described in Part J of Example 1. Chromatography on silica gel (5%–7% methanol in CH2Cl2 gradient) followed by recrystallization from isopropanol afforded 2-ethyl-1-isobutyl-8-(pyridi... | CCc1nc2c(N)nc3ccc(-c4cccnc4)cc3c2n1CC(C)C | null | null | null |
1,045,770 | ord_dataset-dd320ded4b3f4764af39de99491533f7 | null | 2011-01-01T00:04:00 | true | [CH2:1]([OH:16])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][OH:15].[OH-].[K+].[CH2:19](Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>C(Cl)Cl>[CH2:19]([O:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][CH2:2][CH2:1][OH:16])[C:20]1[CH... | OCCOCCOCCOCCOCCO | ClCc1ccccc1 | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | ClCCl | null | null | null | null | null | null | null | null | null | 130 | 0.25 | To Compound 1 (5.2 g, 21.8 mmol), potassium hydroxide (1.2 g, 21.4 mmol) was added; this was followed by stirring on an oil bath at 130° C. for 15 minutes, after which the oil bath was removed and benzyl chloride (2.7 g, 21.3 mmol) was gradually added. This was again heated to 130° C. and stirred for 2 hours. After the... | OCCOCCOCCOCCOCCOCc1ccccc1 | null | 32.9 | null |
1,619,688 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [N+:1]([C:4]1[C:5]([CH:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[OH:15])=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-])=O>[Pd].CCO.CO>[NH2:1][C:4]1[C:5]([CH:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[OH:15])=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2 | O=[N+]([O-])c1c(C(O)c2ccccc2)ccc2cccnc12 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | CCO | null | null | null | null | null | null | null | null | null | null | 1.5 | Palladium on Carbon (10%, 38 mg) was added to a solution of (8-nitro-quinolin-7-yl)-phenyl-methanol (Intermediate 214) (500 mg, 1.78 mmol) in EtOH (20 ml) and the mixture was stirred under an atmosphere of hydrogen for 1.5 h. The mixture was diluted with MeOH (40 ml), filtered through celite and the filtrate was concen... | Nc1c(C(O)c2ccccc2)ccc2cccnc12 | null | 99.4 | null |
1,098,154 | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | null | 2011-01-01T00:10:00 | true | [C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([F:13])=[CH:5][CH:4]=1)#[N:2].[ClH:14]>C(O)C.[Pd]>[ClH:14].[F:13][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([CH2:1][NH2:2])=[CH:4][CH:5]=1 | N#Cc1ccc(F)c2ccccc12 | null | null | [Pd] | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 1-cyano-4-fluoronapthalene (1.05 g, 6.12 mmol) and 1.5 mL of HCl (aq.) in absolute ethanol (50 mL) was stirred under a hydrogen atmosphere (balloon) with 10% palladium on carbon (0.20 g) for 16 hours. The catalyst was removed by filtration through Celite®, and the filtrate concentrated under vacuum. The r... | NCc1ccc(F)c2ccccc12 | null | 44 | null |
230,499 | ord_dataset-67c9ee844bf341888b345c8e36183b40 | null | 1991-01-01T00:07:00 | true | B.[Na].C[O:4][C:5](=O)[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:29])[C@@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17](=[O:28])[CH2:18][CH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][CH2:20]1.Cl>O1CCCC1.CO>[CH:19]1([CH2:18][C:17]([N:13]2[CH2:14][CH2:15][CH2:16][C@H:12]2[C:11]([N:7]2[CH2:8][CH2:9][CH2... | COC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)CC1CCc2ccccc21 | null | null | B | Cl | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | 25 | 15 | 0.57 g of sodium boron hydride was added with stirring to 9 ml of a 80% methanol solution under ice-cooling. To the mixture was added dropwise 1.15 g of 1-[1-(2-indanylacetyl)-L-prolyl]-L-proline methyl ester dissolved in a mixed solution of 5 ml of tetrahydrofuran and 5 ml of methanol. After addition, the mixture was ... | O=C([C@@H]1CCCN1C(=O)CC1CCc2ccccc21)N1CCC[C@H]1CO | null | 68.5 | null |
717,044 | ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | null | 2006-01-01T00:07:00 | true | [NH2:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[H-].[Na+].Cl[C:14]1[N:19]=[C:18]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[N:17]=[C:16]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[N:15]=1.O>CN(C=O)C>[NH2:1][C:2]1[N:6]([C:14]2[N:19]=[C:18]([N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)[N:1... | Clc1nc(N2CCOCC2)nc(N2CCOCC2)n1 | Nc1nc2ccccc2[nH]1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | 25 | 2 | 9.32 g (70 mmol) of 2-aminobenzimidazole dissolved in DMF (300 ml) was added and reacted with 60% sodium hydride (2.80 g, 70 mmol) at room temperature for 30 minutes. This suspension was added to a solution of 14.3 g (50 mmol) of 2-chloro-4,6-dimorpholino-1,3,5-triazine dissolved in DMF (200 ml) and stirred at room tem... | Nc1nc2ccccc2n1-c1nc(N2CCOCC2)nc(N2CCOCC2)n1 | null | 92.6 | null |
1,672,948 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [F:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[NH:10][C:11]1[C:16]([C:17]2[N:25]=[CH:24][N:23]=[C:22]3[C:18]=2[N:19]=[CH:20][N:21]3[CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)=[CH:15][CH:14]=[CH:13][N:12]=1.[F:32][C:33]1[CH:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[C:35]([C:43]([F:46])([F:45])[F:44... | O=S(=O)(Cl)c1ccc(F)cc1C(F)(F)F | Nc1ccc(F)c(Nc2ncccc2-c2ncnc3c2ncn3C2CCCCO2)c1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | ClCCl | null | null | null | null | null | null | null | null | null | 50 | 2 | The 2,6-difluoro-N1-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-yl)benzene-1,3-diamine (20 mg, 0.047 mmol) prepared at Step 9 was added and dissolved into dichloromethane solvent. 4-fluoro-2-(trifluoromethyl)benzenesulfonyl chloride (18 mg, 0.07 mmol) and pyridine (8 uL, 0.094 mmol) were added into the rea... | O=S(=O)(Nc1ccc(F)c(Nc2ncccc2-c2ncnc3c2ncn3C2CCCCO2)c1F)c1ccc(F)cc1C(F)(F)F | null | 89 | null |
186,056 | ord_dataset-754e10d30fb249229e130865010ab25b | null | 1989-01-01T00:03:00 | true | Cl.[CH2:2]([N:4]([CH2:7][CH:8]([OH:29])[CH2:9][NH:10][C:11]([C:13]1[N:14]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:15]2[C:20]([C:21]=1[OH:22])=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:5][CH3:6])[CH3:3].C(N(CC)CC)C.[C:37]([Cl:43])(=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39]>C(Cl)Cl>[ClH:43].[CH2:2]([N:4]([CH... | CC(C)(C)C(=O)Cl | CCN(CC)CC(O)CNC(=O)c1c(O)c2ccccc2n1-c1ccccc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 3 | 12.6 g of 2-[3-(N,N-diethylamino)-2-hydroxypropylaminocarbonyl]-3-hydroxy-1-phenylindole hydrochloride (0.03 mole) are mixed with 150 ml of methylene chloride, 4.2 ml of triethylamine (0.03 mole) and 3.9 ml of pivaloyl chloride (0.03 mole) and the reaction mixture allowed to stand for 3 h at room temperature. The mixtu... | CCN(CC)CC(O)CNC(=O)c1c(OC(=O)C(C)(C)C)c2ccccc2n1-c1ccccc1 | null | null | null |
149,150 | ord_dataset-f222e615b1f74f0fabef9cd9b98516b7 | null | 1986-01-01T00:10:00 | true | C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH:8]([C:10]1[N:11]=[N:12][C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:14]([CH3:16])[N:15]=1)[NH2:9]>C(Cl)Cl>[C:5]([NH:9][NH:8][C:10]1[N:11]=[N:12][C:13]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[C:14]([CH3:16])[N:15]=1)(=[O:7])[CH3:6] | Cc1nc(NN)nnc1-c1ccccc1 | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 0.25 | Acetic anhydride (1.6 g) was added dropwise to a stirred solution of 3-hydrazino-5-methyl-6-phenyl-1,2,4-triazine (3 g) in methylene chloride (30 ml) under ice cooling and then the stirring was continued for 15 minutes. The solution was washed with water, dried over sodium sulfate and concentrated under reduced pressur... | CC(=O)NNc1nnc(-c2ccccc2)c(C)n1 | null | 92.9 | null |
916,813 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | Br[C:2]1[S:3][CH:4]=[C:5]([Cl:7])[CH:6]=1.[Br-].[CH3:9][C:10]1[N:15]=[C:14]([Zn+])[CH:13]=[CH:12][CH:11]=1.C1COCC1>CCOCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:7][C:5]1[CH:6]=[C:2]([C:... | Clc1csc(Br)c1 | Cc1cccc([Zn+])n1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | [Br-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | C1CCOC1 | null | null | null | null | null | null | null | null | null | 40 | null | To a solution of 2-bromo-4-chloro-thiophene (Gronowitz, Rosén Chemica Scripta, 1971, 1, 33) (1.50 g, 7.60 mmol) and 0.5 M solution of 6-methyl-2-pyridylzinc bromide in THF (23.00 mL, 11.39 mmol) is added Pd(PPh3)4 (0.18 g, 0.15 mmol). The solution is heated at 40° C. overnight, diluted with Et2O (50 mL), washed with sa... | Cc1cccc(-c2cc(Cl)cs2)n1 | null | 28 | null |
1,543,258 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [OH:1][CH:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)[C:3]1[CH:4]=[C:5]([C:16](O)=[O:17])[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:8]=1.Cl.Cl.[CH3:27][C:28]1[N:33]=[CH:32][C:31]([C@H:34]([NH2:36])[CH3:35])=[CH:30][CH:29]=1.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC... | Cc1ccc(-c2cc(C(=O)O)cc(C(O)c3ccccn3)c2)cc1 | Cc1ccc([C@@H](C)N)cn1 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | Cl | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 16 | To a solution of 5-(hydroxy-pyridin-2-yl-methyl)-4′-methyl-biphenyl-3-carboxylic acid (25 mg, 0.078 mmol) in N,N-dimethylformamide (1 mL) were added (R)-1-(6-methylpyridin-3-yl)ethanamine dihydrochloride (35 mg, 0.17 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (50 mg, 0.13 mmol), ... | Cc1ccc(-c2cc(C(=O)N[C@H](C)c3ccc(C)nc3)cc(C(O)c3ccccn3)c2)cc1 | null | null | null |
1,093,049 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [Br:1][C:2]1[C:10]2[N:9]=[C:8]([N:11]3[CH2:16][CH2:15][N:14]([C:17]4[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:20]=[CH:19][N:18]=4)[CH2:13][CH2:12]3)[NH:7][C:6]=2[CH:5]=[C:4]([C:27]([F:30])([F:29])[F:28])[CH:3]=1.[CH3:31][Si:32]([CH3:39])([CH3:38])[CH2:33][CH2:34][O:35][CH2:36]Cl>C(Cl)Cl>[Br:1][C:2]1[C:10]2[N:9]=[... | FC(F)(F)c1cc(Br)c2nc(N3CCN(c4ncccc4C(F)(F)F)CC3)[nH]c2c1 | C[Si](C)(C)CCOCCl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | 4-Bromo-6-trifluoromethyl-2-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-1H-benzoimidazole (2 g, 4 mmol, Example 7) in CH2Cl2 (20 mL) reacted with 2-(trimethylsilyl)ethoxymethyl chloride (660 mg, 4 mmol, Aldrich) under the conditions of Example 127a to give the title compound as a light-brown oil. MS (ESI, pos. ... | C[Si](C)(C)CCOCn1c(N2CCN(c3ncccc3C(F)(F)F)CC2)nc2c(Br)cc(C(F)(F)F)cc21 | null | null | null |
7,215 | ord_dataset-653be8036d754ce7b8a1c4cd419eaf55 | null | 1976-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.[CH:12]1([C:15](Cl)=[O:16])[CH2:14][CH2:13]1.N1C=CC=CC=1>CCOCC>[CH:12]1([C:15]([O:11][CH2:10][CH2:9][S:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[O:16])[CH2:14][CH2:13]1 | O=C(Cl)C1CC1 | OCCSc1ccc(Cl)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | CCOCC | null | null | null | null | null | null | null | null | null | 25 | 8 | To a mixture of 1.88 g. 2-(4-chlorophenylthio)ethanol and 1.35 g. cyclopropylcarboxylic acid chloride in 50 ml. ether is added 2 equivalents pyridine. The reaction mixture is stirred overnight at room temperature and worked up as in Example 5 to yield 2-(4-chlorophenylthio)ethyl cyclopropanecarboxylate. | O=C(OCCSc1ccc(Cl)cc1)C1CC1 | null | null | null |
1,680,513 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([Cl:11])[N:3]=1.[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1>C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][O:12]2)=[C:4]([Cl:11])[N:3]=1 | Clc1nc(Cl)c2[nH]cnc2n1 | C1=COCCC1 | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | 50 | null | To 2,6-dichloropurine (25.0 g) (available from, for example, Aldrich, UK) was added ethyl acetate (260 ml), followed by p-toluenesulfonic acid (0.253 g). The mixture was heated to 50° C. and then 3,4-dihydro-2H-pyran (16.8 g) was added. The reaction mixture was then heated at 50° C. for 4 hours. The reaction mixture wa... | Clc1nc(Cl)c2ncn(C3CCCCO3)c2n1 | null | 102.1 | null |
39,229 | ord_dataset-de10a15943a54ac7a3c3e1c774d21392 | null | 1978-01-01T00:04:00 | true | [OH:1][CH2:2][C:3]([CH2:7][OH:8])([CH2:5][OH:6])[CH3:4].[C:9]1([CH3:17])[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=1.C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH3:4][C:3]1([CH2:7][OH:8])[CH2:5][O:6][CH:17]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[O:1][CH2:2]1 | Cc1ccc(C=O)cc1 | CC(CO)(CO)CO | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | O | null | null | null | null | null | null | null | null | null | null | null | 1,1,1-tris(Hydroxymethyl)ethane (12.0 g), p-tolualdehyde (12.0 g), benzene (100 ml) and toluene-p-sulphonic acid (100 mg) were heated under reflux in a Dean and Stark water trap until no more water separated. The benzene was removed and the crude product was crystallised from light petroleum (b.p. 60°-80°) ethyl acetat... | Cc1ccc(C2OCC(C)(CO)CO2)cc1 | null | null | null |
1,479,856 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [NH2:1][C:2]1[C:7]2=[C:8]([C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.[Br:25]N1C(=O)CCC1=O>C(#N)C>[NH2:1][C:2]1[C:7]2=[C:8]([C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)[C:9]([C:11]([O:13][... | CCOC(=O)c1cn2ncnc(N)c2c1-c1ccc([N+](=O)[O-])cc1 | O=C1CCC(=O)N1Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 60 | null | Ethyl 4-amino-5-(4-nitrophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate (2.0 g, 6.11 mmol) was suspended in ACN and treated with N-bromosuccinimide (1.20 g, 6.72 mmol). The dark suspension was heated to 60° C. for 1 h. The suspension was cooled and filtered. The brown solid was washed with ACN and MeOH. The product ... | CCOC(=O)c1c(-c2ccc([N+](=O)[O-])cc2)c2c(N)ncnn2c1Br | null | 83 | null |
242,813 | ord_dataset-fa3b512e2d924b9b965301ebcba6853d | null | 1992-01-01T00:03:00 | true | [O:1]=[C:2]1[CH2:7][S:6][C:5]2[S:8][C:9]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:10][C:4]=2[NH:3]1.ClC1C=C(C=CC=1)C(OO)=[O:20]>C(OCC)(=O)C.C(O)C>[O:1]=[C:2]1[CH2:7][S:6](=[O:20])[C:5]2[S:8][C:9]([S:11](=[O:13])(=[O:14])[NH2:12])=[CH:10][C:4]=2[NH:3]1 | NS(=O)(=O)c1cc2c(s1)SCC(=O)N2 | O=C(OO)c1cccc(Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | 8 | To a mixture of 2,3-dihydro-2-oxo-6-sulfamoyl-1H-thieno[2,3-b][1,4]thiazine (0.25 g, 1 mmol) in ethyl acetate (8 ml) and ethanol (8 ml) was added 3-chloroperoxybenzoic acid (0.43 g, 80-85% pure, 2 mmol). The reaction mixture was stirred overnight and the resulting solid collected, triturated with hot ethyl acetate and ... | NS(=O)(=O)c1cc2c(s1)S(=O)CC(=O)N2 | null | null | null |
845,601 | ord_dataset-e2b35e721c2741999b0005d12691f9fe | null | 2008-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([O:23][C:24]3[CH:25]=[C:26]([Cl:30])[CH:27]=[N:28][CH:29]=3)=[C:16]([CH:22]=2)[C:17]([O:19]CC)=[O:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Li+].[OH-]>CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([O:23][C:24]3[CH:25]=[C... | CCOC(=O)c1cc(NS(=O)(=O)c2ccc(Cl)cc2)ccc1Oc1cncc(Cl)c1 | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | null | 8 | To a stirred solution of the product of Example 8 (81 mg, 0.170 mmol) in MeOH (3 mL) and water (1.0 mL) was added LiOH (89.6 mg, 3.74 mmol). The solution was stirred overnight and the solvent was evaporated to yield a white solid which was recrystallized from chloroform/ethanol. Isolated yield of the title compound: 46... | O=C(O)c1cc(NS(=O)(=O)c2ccc(Cl)cc2)ccc1Oc1cncc(Cl)c1 | null | null | null |
1,148,509 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].[CH2:13]([NH:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>ClCCl>[CH2:13]([N:20]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[S:... | N#Cc1ccc(S(=O)(=O)Cl)cc1 | COc1ccc(CNCc2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 4 | 4-cyanobenzene-1-sulfonyl chloride (600 mg, 3 mmol) was added to a solution of N-benzyl-1-(4-methoxyphenyl)methanamine (example 5-46b, 750 mg, 3.3 mmol) and triethylamine (500 mg, 3.6 mmol) in dichloromethane (15 mL). The reaction was stirred at ambient temperature for 4 hours then concentrated on the rotovap. The crud... | COc1ccc(CN(Cc2ccccc2)S(=O)(=O)c2ccc(C#N)cc2)cc1 | null | null | null |
878,745 | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | null | 2009-01-01T00:05:00 | true | C[O:2][C:3]([CH:5]1[CH2:9][CH:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][N:6]1[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:4].[Li+].[OH-]>C1COCC1.O>[CH2:18]([N:6]1[CH2:7][CH:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][CH:5]1[C:3]([OH:4])=[O:2])[C:... | COC(=O)C1CC(NCc2ccccc2)CN1Cc1ccccc1 | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | null | 8 | 1-Benzyl-4-(benzylamino)-pyrrolidine-2-carboxylic acid methyl ester and LiOH are dissolved in THF/H2O, and then stirred overnight. After removal of solvent, the residue is neutralized to PH=6-7, and then extracted by EA. The organic layer is washed with water and brine, dried, and concentrated to afford 1-benzyl-4-(ben... | O=C(O)C1CC(NCc2ccccc2)CN1Cc1ccccc1 | null | null | null |
983,107 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]([OH:13])[C@H:10]2[OH:11])[OH:9])=[CH:4][C:3]=1[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]#[CH:28])=[CH:23][CH:22]=1.I[C:30]1[CH:35]=[N:34][CH:33]=[CH:32][N:31]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:17][C@H:16]([CH2:1... | Ic1cnccn1 | C#Cc1ccc(Cc2cc([C@@]3(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)ccc2Cl)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The compound was obtained starting from 1-chloro-4-(β-D-glucopyranos-1-yl)-2-(4-ethynyl-benzyl)-benzene and iodo-pyrazine. | OC[C@H]1O[C@](O)(c2ccc(Cl)c(Cc3ccc(C#Cc4cnccn4)cc3)c2)[C@H](O)[C@@H](O)[C@@H]1O | null | null | null |
1,140,812 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | C(OC(=O)[NH:7][C:8]1([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][C:28]3[CH:38]=[CH:37][C:31]4[O:32][C:33]([F:36])([F:35])[O:34][C:30]=4[CH:29]=3)=[C:20]([C:39]([F:42])([F:41])[F:40])[CH:19]=2)[CH2:13][O:12]C(C)(C)[O:10][CH2:9]1)(C)(C)C.[ClH:44]>C(O)C>[ClH:44].[NH2:7][C:8]([CH2:16][CH2:17... | CC(C)(C)OC(=O)NC1(CCc2ccc(OCCCc3ccc4c(c3)OC(F)(F)O4)c(C(F)(F)F)c2)COC(C)(C)OC1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 80 | 1.5 | Compound 87-4 (870 mg) was dissolved in ethanol (15 ml), concentrated hydrochloric acid (1.5 ml) was added, and the mixture was stirred at 80° C. for 1.5 hr. The reaction mixture was concentrated, and the residue was washed with diethyl ether to give the object product (510 mg) as a white powder. | NC(CO)(CO)CCc1ccc(OCCCc2ccc3c(c2)OC(F)(F)O3)c(C(F)(F)F)c1 | null | null | null |
861,695 | ord_dataset-93908aaae836460ebd48d733eccad483 | null | 2009-01-01T00:01:00 | true | [CH3:1][O:2][C:3]([C:5]1[C:6]([O:13][CH3:14])=[N:7][C:8](Cl)=[N:9][C:10]=1[CH3:11])=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH2:21]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][CH3:30])[C:24]=1B(O)O)[CH3:22]>COCCOC.O>[CH3:1][O:2][C:3]([C:5]1[C:6]([O:13][CH3:14])=[N:7][C:8]([C:24]2[C:25]([CH2:29][CH3:30])=[CH:26][CH:27]=[CH:2... | COC(=O)c1c(C)nc(Cl)nc1OC | CCc1cccc(CC)c1B(O)O | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | O | null | null | null | null | null | null | null | null | null | 95 | 18 | To a solution of 2-chloro-4-methoxy-6-methyl-pyrimidine-5-carboxylic acid methyl ester (4.1 g, 19.0 mmol) in DME (100 mL) is added potassium carbonate (10.5 g, 76 mmol, 4 eq) in water (40 mL) followed by 2,6-diethylphenylboronic acid (6.77 g, 38 mmol, 2 eq). The resulting mixture is degassed by bubbling with argon for ... | CCc1cccc(CC)c1-c1nc(C)c(C(=O)OC)c(OC)n1 | null | null | null |
487,365 | ord_dataset-7b02d32cc502407f94aea8e5caf405a2 | null | 2000-01-01T00:12:00 | true | [C:1]1([C:7]2[NH:8][CH:9]=[C:10]([CH2:12]O)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[N:16][C:15]=1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(N(CC)CC)C>S(Cl)(Cl)=O>[C:1]1([C:7]2[NH:11][C:10]([CH2:12][N:27]3[CH2:28][CH2:29][N:24]([C:15]4[N:16]=[CH:17... | OCc1c[nH]c(-c2ccccc2)n1 | c1ccc2nc(N3CCNCC3)ncc2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=S(Cl)Cl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 0.17 | A sample of 2-phenyl-4-hydroxymethylimidazole (348 mg, 2 mmol) is heated for 5 min in thionyl chloride (5 mL) and subsequently concentrated. Chloroform (10 mL) is added and the solution reconcentrated. The resulting dark oil is then taken up in chloroform (10 mL) and treated with 1-quinazolin-2-ylpiperazine (428 mg, 2 ... | c1ccc(-c2ncc(CN3CCN(c4ncc5ccccc5n4)CC3)[nH]2)cc1 | null | 86.4 | null |
863,422 | ord_dataset-b8b98725045d45bdbd73512048f4b47e | null | 2009-01-01T00:02:00 | true | [CH2:1]([O:8][C:9]1[CH:20]=[CH:19][C:12]([CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([O:23][C@H:24]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:25][C:26]1[CH:36]=[CH:35][C:29]([O:30][CH2:31][C:32](O)=[O:33])=[CH:28][CH:27]=1)[CH3:22].C(N(CC)C(C)C)(C... | CCCCNCc1ccc(OCc2ccccc2)cc1 | CCOC(=O)[C@H](Cc1ccc(OCC(=O)O)cc1)OCC | null | CN(C)C(On1nnc2ccccc21)=[N+](C)C | F[B-](F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of N-[4-(benzyloxy)benzyl]-N-butylamine (3.59 g, 12.0 mmol) and {4-[(2S)-2,3-diethoxy-3-oxopropyl]phenoxy}acetic acid (2.96 g, 10.0 mmol) in methylene chloride (100 mL) were added N,N-diisopropylethylamine (4.00 mL, 23.0 mmol) and O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (3.85 ... | CCCCN(Cc1ccc(OCc2ccccc2)cc1)C(=O)COc1ccc(C[C@H](OCC)C(=O)OCC)cc1 | null | 32.9 | null |
766,816 | ord_dataset-7a8649d55889427e85b208ae89475895 | null | 2007-01-01T00:04:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([CH:22]([OH:24])[CH3:23])=[CH:14][CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([C@H:22]([... | CC(O)c1ccc2c(n1)N1[C@H](C2)CN(C(=O)OC(C)(C)C)C[C@H]1C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | A solution of 3.09 g (9.27 mmol) (4R,9aR)-6-(1-(RS)-hydroxy-ethyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 33 mL dichloromethane was cooled to 0 deg C. and treated with 8.8 mL (12.7 g, 0.11 mol) trifluoroacetic acid. The cooling bath was removed and the volatile comp... | C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc([C@@H](C)O)nc3N21 | null | null | null |
911,483 | ord_dataset-c663259b80f947e2a8923796fb0e9a6b | null | 2009-01-01T00:10:00 | true | [CH:1]([S:4]([C:7]1[CH:8]=[C:9]([NH2:21])[C:10]([NH:13][CH2:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[CH:11][CH:12]=1)(=[O:6])=[O:5])([CH3:3])[CH3:2].[C:22](Cl)(=O)[C:23]([CH3:26])([CH3:25])[CH3:24]>>[C:23]([C:26]1[N:13]([CH2:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:10]2[CH:11]=[CH:12][C:7]([S:4... | CC(C)S(=O)(=O)c1ccc(NCC2CCOCC2)c(N)c1 | CC(C)(C)C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared according to the procedure described in Step C of Example 17 from 4-(isopropylsulfonyl)-N′-(tetrahydro-2H-pyran-4-ylmethyl)benzene-1,2-diamine (Step B) and pivaloyl chloride. | CC(C)S(=O)(=O)c1ccc2c(c1)nc(C(C)(C)C)n2CC1CCOCC1 | null | null | null |
1,501,611 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][C:11]2[CH:12]=[C:13]([NH:17][C:18]3[C:23]([Cl:24])=[CH:22][N:21]=[C:20](Cl)[N:19]=3)[CH:14]=[CH:15][CH:16]=2)[CH:5]=[CH:6][CH:7]=1.Cl>COCCO.C(O)C>[Cl:24][C:23]1[CH:22]=[N:21][C:20]2[NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[C:4]([CH:3]=3)[CH2:8][CH2:9][CH2:10][C:11]3[CH:12]=[C:13]... | Nc1cccc(CCCc2cccc(Nc3nc(Cl)ncc3Cl)c2)c1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCO | CCO | null | null | null | null | null | null | null | null | null | 150 | null | N-{3-[3-(3-Aminophenyl)propyl]phenyl}-2,5-dichloropyrimidin-4-amine (20 mg, 0.05 mmol) was stirred in 2-methoxyethanol (1.0 mL) and a solution of hydrogen chloride in ethanol (0.75 mL, 3.5 M). The mixture was heated to 150° C. for 30 minutes in a microwave. Purification by preparative LCMS gave the desired product (6.5... | Clc1cnc2nc1Nc1cccc(c1)CCCc1cccc(c1)N2 | null | 38.6 | null |
894,266 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | [Cl:1][C:2]1[C:15]([Cl:16])=[CH:14][C:5]2[NH:6][C:7]([CH2:9][C:10]([F:13])([F:12])[F:11])=[N:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:23][C:24]([F:35])([F:34])[S:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=1>CN(C=O)C>[Cl:16][C:15]1[C:2]([Cl:1])=[CH:3][C:4]2[N:8]([CH2:30][C:29]3[CH:32]=[CH:33][C:26]... | FC(F)(F)Cc1nc2cc(Cl)c(Cl)cc2[nH]1 | FC(F)(F)Sc1ccc(CBr)cc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To 5,6-dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzimidazole (434 mg) in DMF (5 mL) was added potassium carbonate powder (669 mg) and 4-(trifluoromethylthio) benzyl bromide (596 mg). The resulting mixture was stirred at room temperature overnight. The reaction mixture was quenched with water, extracted with EtOAc, and dr... | FC(F)(F)Cc1nc2cc(Cl)c(Cl)cc2n1Cc1ccc(SC(F)(F)F)cc1 | null | null | null |
66,144 | ord_dataset-8af141577c90485cb9c91079a5ef96b3 | null | 1980-01-01T00:05:00 | true | [CH2:1]([O:3][N:4]=[C:5]([C:11]1[N:12]=[C:13]([OH:16])[S:14][CH:15]=1)[C:6]([O:8]CC)=[O:7])[CH3:2].C(O)C.[OH-].[K+].Cl>O>[CH2:1]([O:3][N:4]=[C:5]([C:11]1[N:12]=[C:13]([OH:16])[S:14][CH:15]=1)[C:6]([OH:8])=[O:7])[CH3:2] | CCON=C(C(=O)OCC)c1csc(O)n1 | null | null | Cl | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | null | null | To a solution of 10 g. of ethyl α-ethoxyimino-(2-hydroxythiazol-4-yl)acetate in 30 ml. of ethanol is added a solution of 11.47 g. of KOH in 50 ml. of water at room temperature and the mixture is stirred for 25 minutes. The reaction mixture is condensed under reduced pressure and is made acidic with 10% aq. HCl. Ethyl a... | CCON=C(C(=O)O)c1csc(O)n1 | null | null | null |
1,762,395 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [OH-].[Na+].[OH:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1.Br[CH:14]([OH:17])[CH2:15][CH3:16]>CCO>[OH:17][CH2:14][CH2:15][CH2:16][O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1 | O=C(O)c1ccc(O)cc1 | CCC(O)Br | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | An aqueous solution of NaOH (1 mol) and KI (0.05 mmol) was added to a solution of 4-hydroxybenzoic acid (0.5 mmol) and 400 mL EtOH solution under a nitrogen atmosphere and stirred. After stirring for 30 minutes, an EtOH solution including bromopropanol (0.55 mmol) was dropped thereinto, and then, reacted for 24 hours a... | O=C(O)c1ccc(OCCCO)cc1 | null | null | null |
1,281,216 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [OH:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][CH:13]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:6]3=[CH:5][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH:37]([CH3:39])[CH3:38])=[C:32]([C:40]([F:43])([F:42])[F:41])[CH:31]=1>CC(N(C)C)=O>[CH:37]... | CC(C)Oc1ccc(CCl)cc1C(F)(F)F | CC(C)(C)OC(=O)CC1CCn2c1cc1cc(O)ccc12 | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)N(C)C | null | null | null | null | null | null | null | null | null | null | 80 | 16 | To a mixture of tert-butyl 2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (1.86 mmol) and cesium carbonate (2.8 mmol) in DMA (7.45 mL) was added 4-(chloromethyl)-1-isopropoxy-2-(trifluoromethyl)benzene (1.96 mmol). The reaction was stirred at 80° C. for 16 h. The mixture was filtered through Celite®. The ... | CC(C)Oc1ccc(COc2ccc3c(c2)cc2n3CCC2CC(=O)OC(C)(C)C)cc1C(F)(F)F | null | null | null |
1,626,467 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](=[O:17])[CH2:13][CH:14]([CH3:16])[CH3:15])=[C:5]2O.P(Cl)(Cl)([Cl:21])=O.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](=[O:17])[CH2:13][CH:14]([CH3:16])[CH3:15])=[C:5]2[Cl:21] | CC(C)CC(=O)c1cnc2ccc(Br)cc2c1O | O=P(Cl)(Cl)Cl | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | 85 | 1 | 1-(6-Bromo-4-hydroxyquinolin-3-yl)-3-methylbutan-1-one (300 mg, 0.970 mmol) was added to phosphoryl chloride (9.7 mL) and the reaction was stirred at 85° C. for 1 h. After this time the reaction mixture was cooled to room temperature and slowly poured into a 2:1 solution of satd. aq. sodium bicarbonate/ethyl acetate th... | CC(C)CC(=O)c1cnc2ccc(Br)cc2c1Cl | null | 98 | null |
896,711 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH:5]=[C:4]([NH:14][C:15]2[CH:19]=[CH:18][NH:17][N:16]=2)[N:3]=1.[C:20]1([OH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH3:13][O:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2]([O:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[N:3][C:4]([NH... | Oc1ccccc1 | COc1ccc2c(Cl)nc(Nc3cc[nH]n3)cc2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Similar procedure as described in example 10 was used, starting from (1-chloro-6-methoxy-isoquinolin-3-yl)-(1H-pyrazol-3-yl)-amine and phenol to give (6-methoxy-1-phenoxy-isoquinolin-3-yl)-(1H-pyrazol-3-yl)-amine. LC-MS m/e 333(MH+). | COc1ccc2c(Oc3ccccc3)nc(Nc3cc[nH]n3)cc2c1 | null | null | null |
1,019,541 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | [OH:1][CH2:2][C:3]1[CH:4]=[C:5]([S:9][C:10]2[CH:11]=[N:12][CH:13]=[C:14]([CH:17]=2)[C:15]#[N:16])[CH:6]=[CH:7][CH:8]=1.[CH2:18]([C:20]1[C:21]([OH:30])=[C:22]([C:27](=[O:29])[CH3:28])[CH:23]=[CH:24][C:25]=1O)[CH3:19]>>[C:27]([C:22]1[CH:23]=[CH:24][C:25]([O:1][CH2:2][C:3]2[CH:4]=[C:5]([S:9][C:10]3[CH:11]=[N:12][CH:13]=[C... | N#Cc1cncc(Sc2cccc(CO)c2)c1 | CCc1c(O)ccc(C(C)=O)c1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using the method of Preparation 160 using 5-(3-(hydroxymethyl)phenylthio) nicotinonitrile (3.90 g, 16.1 mmol) and 1-(3-ethyl-2,4-dihydroxyphenyl)ethanone (2.90 g, 16.1 mmol) affords the title compound (2.20 g, 34%): 1H NMR (CDCl3) δ 1.10 (t, J=7.4 Hz, 3H), 2.57 (s, 3H), 2.71 (q, J=7.4 Hz, 2H), 5.18 (s, 2H), 6.43 (d, J=... | CCc1c(OCc2cccc(Sc3cncc(C#N)c3)c2)ccc(C(C)=O)c1O | null | 33.8 | null |
576,448 | ord_dataset-f4512fe8cd804ac79da66cbc0c2b9d42 | null | 2002-01-01T00:12:00 | true | C(OC([NH:8][C:9]1[CH:10]=[C:11]([S:17]([NH2:20])(=[O:19])=[O:18])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])=O)(C)(C)C.[Cl:21][C:22]1[CH:23]=[C:24]([NH:38][C:39](OC2C=CC=CC=2)=[O:40])[C:25](=[CH:36][CH:37]=1)[C:26](OCC1C=CC=CC=1)=[O:27]>>[NH2:8][C:9]1[CH:10]=[C:11]([S:17]([N:20]2[C:26](=[O:27])[C:25]3[C:24](=[CH:23][C:22]([... | O=C(Nc1cc(Cl)ccc1C(=O)OCc1ccccc1)Oc1ccccc1 | COc1ccc(S(N)(=O)=O)cc1NC(=O)OC(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 400 mg (1.40 mmol) of 3-t-butoxycarbonylamino-4-methoxybenzenesulfonamide and 533 mg (1.40 mmol) of benzyl 4-chloro-2-N-phenoxycarbonylanthranilate were treated in the same way as in Preparation Example 17 to obtain 86 mg (yield 16%: 4 steps) of the above-identified compound. Properties: colorless crystal, Melting poin... | COc1ccc(S(=O)(=O)n2c(=O)[nH]c3cc(Cl)ccc3c2=O)cc1N | null | 16 | null |
1,073,970 | ord_dataset-5df93261afc143c3ae919a57ff4fc1d4 | null | 2011-01-01T00:07:00 | true | [Br:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([C:11]([OH:13])=O)[CH:10]=2)[CH:7]=1.[F:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH:21]([C:25]([F:28])([F:27])[F:26])[NH:20][CH2:19][CH2:18]2>>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([C:11]([N:20]3[CH2:19][CH2:18][C:17]4[C:22](=[CH:23][CH:24]=[C:15]([F:1... | Fc1ccc2c(c1)CCNC2C(F)(F)F | O=C(O)c1cc2ncc(Br)cn2n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In close analogy to the procedure described in Example 1, 6-bromo-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid is reacted with 6-fluoro-1-trifluoromethyl-1,2,3,4-tetrahydro-isoquinoline to provide the title compound in moderate yield. | O=C(c1cc2ncc(Br)cn2n1)N1CCc2cc(F)ccc2C1C(F)(F)F | null | null | null |
652,283 | ord_dataset-fe016e2f90e741a590ad77fd5933161f | null | 2004-01-01T00:11:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH:10]([CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19][OH:20]>>[OH:20][CH2:19][C:18]1[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=1[NH:16][CH:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O... | CC1CN(C(=O)OC(C)(C)C)CCC1=O | Nc1ccccc1CO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The product was prepared from N-tert-butoxycarbonyl-3-methyl-4-piperidone (4.3 g) and 2-amino-benzyl alcohol (2.59 g) using the method of example 7 step (i). Yield 6.3 g as a mixture of diastereoisomers. | CC1CN(C(=O)OC(C)(C)C)CCC1Nc1ccccc1CO | null | null | null |
271,156 | ord_dataset-a20aed058d7b40bc81fdf50bc5b03f97 | null | 1993-01-01T00:06:00 | true | [F-].[K+].[CH2:3]([C:7]1[CH:12]=[CH:11][C:10]([C:13](=[CH:17][Si](CC)(CC)CC)[C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1)[CH:4]([CH3:6])[CH3:5].O>C(#N)C>[CH2:3]([C:7]1[CH:8]=[CH:9][C:10]([C:13](=[CH2:17])[C:14]([OH:16])=[O:15])=[CH:11][CH:12]=1)[CH:4]([CH3:6])[CH3:5] | CC[Si](C=C(C(=O)O)c1ccc(CC(C)C)cc1)(CC)CC | null | null | [F-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | O | null | null | null | null | null | null | null | null | null | 25 | null | This desilylation (elimination) reaction may be performed, for example, by following the procedure of T. H. Chan et al. referred to above. A catalyst such as, for example, potassium fluoride is used for desilylation. α-(4'-isobutylphenyl)-β-triethylsilyl acrylic acid from Example 4 (0.02 mol) is dissolved in a suitable... | C=C(C(=O)O)c1ccc(CC(C)C)cc1 | null | null | null |
1,258,453 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | [O:1]=[C:2]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:3][C:4]([O:6][CH3:7])=[O:5].C([O-])(=O)C.[Na+].[CH3:18][S:19]([C:22]1[CH:27]=[CH:26][C:25]([N+:28]#[N:29])=[CH:24][CH:23]=1)(=[O:21])=[O:20]>C(O)C.O>[CH3:18][S:19]([C:22]1[CH:23]=[CH:24][C:25]([NH:28]/[N:29]=[C:8](\[C:2](=[O:1])[CH2:3][C:4]([O:6][CH3:7])=[O:5])/[C:9]... | COC(=O)CC(=O)CC(=O)OC | CS(=O)(=O)c1ccc([N+]#N)cc1 | null | CC(=O)[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | 25 | 1 | To a mixture of dimethyl 3-oxopentanedioate (3.48 g, 20 mmol) in ethanol (12 mL) and water (40 mL) at room temperature was added sodium acetate (12.0 g, 146 mmol), and was followed by addition of 4-(methylsulfonyl)benzenediazonium solution (20 mmol). The resulting reaction mixture was stirred at room temperature for 1 ... | COC(=O)CC(=O)/C(=N\Nc1ccc(S(C)(=O)=O)cc1)C(=O)OC | null | 98.2 | null |
1,647,285 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | [C:1]([N:4](C(C)(C)C)[S:5]([C:8]1[CH:9]=[C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([NH2:27])(=[O:26])=[O:25])[CH:19]=2)[C:11]([O:16]C)=[C:12]([CH:14]=[O:15])[CH:13]=1)(=[O:7])=[O:6])(=[O:3])[CH3:2]>ClCCl>[C:1]([NH:4][S:5]([C:8]1[CH:9]=[C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([NH2:27])(=[O:26])=[O:25])... | COc1c(C=O)cc(S(=O)(=O)N(C(C)=O)C(C)(C)C)cc1-c1cccc(S(N)(=O)=O)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 1 | N-acetyl-N-tert-butyl-5-formyl-6-methoxy-biphenyl-3,3′-disulfonamide (100 mg, 0.21 mmol), prepared as in Reference 19, was dissolved in dichloromethane (10 mL). The solution was flushed with nitrogen for 5 minutes and then boron tribromide (1.0 mL, 1M solution in dichloromethane) was added. The mixture was stirred at r... | CC(=O)NS(=O)(=O)c1cc(C=O)c(O)c(-c2cccc(S(N)(=O)=O)c2)c1 | null | 88.4 | null |
448,827 | ord_dataset-a4f0b79f6b9847168861270b79f84afa | null | 1999-01-01T00:11:00 | true | [Br:1][C:2]1[N:7]=[C:6]([C:8]([NH2:10])=[O:9])[CH:5]=[C:4]([N+]([O-])=O)[CH:3]=1.[K].[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([SH:24])=[CH:20][CH:19]=1)([O-:17])=[O:16]>CN(C)C=O>[Br:1][C:2]1[N:7]=[C:6]([C:8]([NH2:10])=[O:9])[CH:5]=[C:4]([S:24][C:21]2[CH:22]=[CH:23][C:18]([N+:15]([O-:17])=[O:16])=[CH:19][CH:20]=2)[CH:3]=1 | NC(=O)c1cc([N+](=O)[O-])cc(Br)n1 | O=[N+]([O-])c1ccc(S)cc1 | null | [K] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 18 | 0.25 g (0.001 mol) of 6-bromo-4-nitropyridine-2-carboxamide was dissolved in 5 ml of dimethylformamide, treated with 0.19 g (0.001 mol) of 4-nitrothiophenol potassium salt and stirred at room temperature for 18 hrs. The reaction mixture was partitioned in water and ethyl acetate and the organic phase was washed with wa... | NC(=O)c1cc(Sc2ccc([N+](=O)[O-])cc2)cc(Br)n1 | null | 87.5 | null |
1,490,360 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[C:12]([C:14]2[CH:19]=[N:18][CH:17]=[C:16]([C:20]3[CH:21]=[N:22][N:23]([CH2:25][CH2:26][O:27]C4CCCCO4)[CH:24]=3)[N:15]=2)[CH:11]=[CH:10][N:9]=1.Cl>O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[C:12]([C:14]2[N:15]=[C:16]([C:20]3[CH:21]=[N:22... | Fc1ccccc1-c1cc(-c2cncc(-c3cnn(CCOC4CCCCO4)c3)n2)ccn1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | 680 mg of the above prepared 2-[2-(2-fluoro-phenyl)-pyridin-4-yl]-6-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-pyrazol-4-yl}-pyrazine are dissolved in 12 ml dioxane. 1.1 l of HCl in dioxane (4 mol/l) is added. The product precipitates from the solution and is filtered. 147 mg of 2-(4-{6-[2-(2-fluoro-phenyl)-pyridin-4-y... | OCCn1cc(-c2cncc(-c3ccnc(-c4ccccc4F)c3)n2)cn1 | null | null | null |
1,264,017 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:18])=[C:6]([C@:8]2([CH3:17])[C:13]([F:15])([F:14])[CH2:12][O:11][C:10]([NH2:16])=[N:9]2)[CH:7]=1.[Cl:19][C:20]1[C:21]([C:27](O)=[O:28])=[N:22][CH:23]=[C:24]([Cl:26])[CH:25]=1>>[NH2:16][C:10]1[O:11][CH2:12][C:13]([F:14])([F:15])[C@:8]([C:6]2[CH:7]=[C:2]([NH:1][C:27]([C:21]3[C:20]([Cl:1... | C[C@]1(c2cc(N)ccc2F)N=C(N)OCC1(F)F | O=C(O)c1ncc(Cl)cc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The condensation of (R)-4-(5-amino-2-fluoro-phenyl)-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine (intermediate XI-1) and 3,5-dichloro-pyridine-2-carboxylic acid following procedure I yielded the title compound as a colorless solid. MS (ISP): m/z=433.2 [M+H]+. | C[C@]1(c2cc(NC(=O)c3ncc(Cl)cc3Cl)ccc2F)N=C(N)OCC1(F)F | null | null | null |
839,078 | ord_dataset-074f86301ec5441ab3b52d902ac06949 | null | 2008-01-01T00:09:00 | true | FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[C:9]([CH3:16])[CH:8]=1)(=O)=O.[N+:19]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)([O-:21])=[O:20].C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>C1(C)C=CC=CC=1>[CH3:16][C:9]1[CH:8]=[C:7]([C:25]2[CH:26]=[CH:27][C:22]([N+:19]([O-:21])=[O:20])=[CH:23][CH:24]... | O=[N+]([O-])c1ccc(B(O)O)cc1 | CC(=O)c1ccc(OS(=O)(=O)C(F)(F)F)cc1C | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 85 | 8 | A mixture of 4-acetyl-3-methylphenyl trifluoromethanesulfonate (6.90 g, 24.0 mmol), 4-nitrophenylboronic acid (3.80 g, 24 mmol), 2 N aqueous sodium carbonate (88.0 mL), dioxane (88.0 mL), and toluene (296 mL) was purged with argon for 30 minutes before [1,1′-bis(diphenyl-phosphino)-ferrocene]dichloro palladium(II) (1:1... | CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1C | null | 99.9 | null |
1,047,170 | ord_dataset-dd320ded4b3f4764af39de99491533f7 | null | 2011-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[S:9](Cl)(=[O:11])=[O:10].Cl.Cl.[NH:15]1[CH2:20][CH2:19][CH:18]([CH2:21][N:22]2[CH2:31][CH2:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:23]2)[CH2:17][CH2:16]1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[S:9]([N:15]... | O=S(=O)(Cl)c1cc(Cl)ccc1Cl | c1ccc2c(c1)CCN(CC1CCNCC1)C2 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 25 | 8 | 2,5-dichlorobenzene-1-sulfonyl chloride (108.1 mg, 0.44 mmol) was added to a solution of 2-(piperidin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline dihydrochloride (92.1 mg, 0.40 mmol) and N,N-diisopropylethylamine (206.9.2 mg, 1.60 mmol) in CH2Cl2 (10 mL) and the mixture was stirred overnight at room temperature. The res... | O=S(=O)(c1cc(Cl)ccc1Cl)N1CCC(CN2CCc3ccccc3C2)CC1 | null | 131.8 | null |
987,588 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | C(CN)O.C([O:12][C:13]1[CH:14]=[C:15]([C:24](=[O:28])[CH:25](O)O)[C:16]2[O:21][CH2:20][C:19](=[O:22])[NH:18][C:17]=2[CH:23]=1)C1C=CC=CC=1.[Br:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][C:37]([NH2:40])([CH3:39])[CH3:38])=[CH:32][CH:31]=1>>[Br:29][C:30]1[CH:31]=[CH:32][C:33]([CH2:36][C:37]([NH:40][CH2:25][CH:24]([C:15]2[C:1... | CC(C)(N)Cc1ccc(Br)cc1 | O=C1COc2c(cc(OCc3ccccc3)cc2C(=O)C(O)O)N1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | NCCO | null | null | null | null | null | null | null | null | null | null | null | null | The preparation of the ethanolamine and debenzylation were carried out as described in Example 19 from 300 mg (0.91 mmol) of 6-benzyloxy-8-(2,2-dihydroxy-acetyl)-4H-benzo[1,4]oxazin-3-one and 250 mg (1.09 mmol) of 2-(4-bromophenyl)-1,1-dimethylethylamine. Beige solid. Yield: 54 mg (14%); mass spectrometry: [M+H]+=435, ... | CC(C)(Cc1ccc(Br)cc1)NCC(O)c1cc(O)cc2c1OCC(=O)N2 | null | null | null |
46,446 | ord_dataset-becaf7dc22c44672b22e4b94335cbf08 | null | 1978-01-01T00:09:00 | true | [CH3:1][C:2]1[NH:3][N:4]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5](=[O:7])[CH:6]=1.[C:17](OC(=O)C)(=[O:19])[CH3:18].C([O-])(=O)C.[Na+]>>[C:17]([O:7][C:5]1[N:4]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=[C:2]([CH3:1])[CH:6]=1)(=[O:19])[CH3:18] | CC(=O)OC(C)=O | Cc1cc(=O)n(CCOc2ccccc2)[nH]1 | null | CC(=O)[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 0.1 mol (21.8 g) of 3-methyl-1-(β-phenoxyethyl)-5-pyrazolone was heated with 0.2 mol (20.4 g) of acetic anhydride in the presence of 0.11 mol (8.2 g) of sodium acetate for 2 hours. | CC(=O)Oc1cc(C)nn1CCOc1ccccc1 | null | null | null |
1,134,110 | ord_dataset-aaeaab5f3720492494c1cbbdd0ed2820 | null | 2012-01-01T00:02:00 | true | [CH:1]1([NH:7][C:8]2[C:12]3([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[N:11]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=3)[C:10](=[O:25])[N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[CH:35]([C:37]1[CH:38]=[C:39]([CH2:43][CH:44]([CH3:47])[C:45]#[N:46])[CH:40]=[CH:41][CH:42]=1)=O.C(O[BH-](OC(=O)C)... | O=C1N=C(NC2CCCCC2)C2(CCNCC2)N1c1cccc(F)c1 | CC(C#N)Cc1cccc(C=O)c1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 0.17 | To a 20 mL dichloroethane solution of 0.35 g (0.92 mmol) 4-(cyclohexylamino)-1-(3-fluorophenyl)-1,3,8-triazaspiro[4.5]dec-3-en-2-one and 0.25 mL (1.4 mmol) DIEA went 0.16 g (0.92 mmol) 3-(3-formylphenyl)-2-methylpropanenitrile (9-3). The suspension was allowed to stir for 10 min then 0.4 g (1.9 mmol) sodium triacetoxyb... | CC(C#N)Cc1cccc(CN2CCC3(CC2)C(NC2CCCCC2)=NC(=O)N3c2cccc(F)c2)c1 | null | null | null |
584,127 | ord_dataset-cb5dd7a8b94e4f19a9148a1904b0dcb6 | null | 2003-01-01T00:03:00 | true | [CH3:1][NH:2][CH2:3][CH2:4][N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][O:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2.S(O[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)(=O)(=O)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(#N)C>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][CH2:25][N:... | CS(=O)(=O)OCCc1ccc(Cl)cc1 | CNCCN1c2ccccc2COc2ccccc21 | null | O=C([O-])[O-] | [I-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 70 | 22 | 5,11-Dihydro-5-[2-(N-methylamino)ethyl]dibenzo[b,e][1,4]oxazepine (254 mg, 1.00 mmol), 4-chlorophenethyl mesylate (352 mg, 1.50 mmol), sodium carbonate (160 mg, 1.50 mmol) and sodium iodide (20 mg, 0.13 mmol) were added to acetonitrile (25 ml), and they were heated at 70° C. under stirring for 22 hours and then at 90° ... | CN(CCc1ccc(Cl)cc1)CCN1c2ccccc2COc2ccccc21 | null | null | null |
1,661,048 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [C:1]([C:3](=[CH:9][C:10]1[CH:11]=[N:12][C:13]([NH:16][C:17]2[N:18]=[C:19]3[C:25]([C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:24][N:23](COCC[Si](C)(C)C)[C:20]3=[N:21][CH:22]=2)=[CH:14][CH:15]=1)[C:4]([N:6]([CH3:8])[CH3:7])=[O:5])#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([C:3](=[CH:9][C:10]1[CH:11]=[N:12][C:13]([... | CN(C)C(=O)C(C#N)=Cc1ccc(Nc2cnc3c(n2)c(C(=O)C(C)(C)C)cn3COCC[Si](C)(C)C)nc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 16 | To a 25 ml one necked round bottom flask 2-cyano-N,N-dimethyl-3-(6-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)pyridin-3-yl)acrylamide (0.1 g, 0.000182 mole) was taken in CH2Cl2 (10 ml). To this reaction mixture TFA (2.0 ml) was added dropwise at 0° C. After completion of the add... | CN(C)C(=O)C(C#N)=Cc1ccc(Nc2cnc3[nH]cc(C(=O)C(C)(C)C)c3n2)nc1 | null | 52.6 | null |
680,451 | ord_dataset-3947f3e1be17462c8f7c7e6ea6e57d0a | null | 2005-01-01T00:08:00 | true | C([O:5][P:6]([O:39]C(C)(C)C)([O:8][CH:9]([CH3:38])[CH2:10][O:11][C:12]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23]([F:26])([F:25])[F:24])[CH:21]=2)[C@@:16]([C:28]2[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=2[O:35][CH3:36])([F:27])[C:15]1=[O:37])=[O:13])=[O:7])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[P:6]([O:8][CH:9]([CH3... | COc1ccc(Cl)cc1[C@]1(F)C(=O)N(C(=O)OCC(C)OP(=O)(OC(C)(C)C)OC(C)(C)C)c2cc(C(F)(F)F)ccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | A solution of (S)-3-(5-chloro-2-methoxy-phenyl)-3-fluoro-2-oxo-6-trifluoromethyl-2,3-dihydro-indole-1-carboxylic acid 2-(di-tert-butoxy-phosphoryloxy)-propyl ester ((S)-VII, n=2) (540 mg, 0.82 mmol) in dichloromethane (30 mL) was stirred with trifluoroacetic acid (0.6 mL) at room temperature for 3 hours. LC-MS indicate... | COc1ccc(Cl)cc1[C@]1(F)C(=O)N(C(=O)OCC(C)OP(=O)(O)O)c2cc(C(F)(F)F)ccc21 | null | 57.4 | null |
1,495,696 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:20]([N:23]1[C:31]2[C:26](=[CH:27][C:28]([C:32](=O)[CH2:33]Br)=[CH:29][CH:30]=2)[CH2:25][CH2:24]1)(=[O:22])[CH3:21]>C(#N)C>[C:20]([N:23]1[C:31]2[C:26](=[CH:27][C:28]([CH2:32][CH2:33][N:11]3[CH2:12... | CC(=O)N1CCc2cc(C(=O)CBr)ccc21 | CC(C)(C)OC(=O)N1CCNCC1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 70 | null | To a solution of piperazine-1-carboxylic acid tert-butyl ester (0.750 g, 4.03 mmol) in dry acetonitrile (20 mL) grounded potassium carbonate (0.486 mL, 8.05 mmol) was added followed by the product mixture from Example 38a (1.134 g) and the reaction was heated at 70° C. under argon over night. The acetonitrile was evapo... | CC(=O)N1CCc2cc(CCN3CCN(C(=O)OC(C)(C)C)CC3)ccc21 | null | 54.8 | null |
1,565,720 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:11]=[C:10](Cl)[C:9]2[C:4](=[C:5]([CH3:15])[C:6]([O:13][CH3:14])=[CH:7][CH:8]=2)[N:3]=1.ClC1C=C([O:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)C2C(=C(Cl)C(OC)=CC=2)N=1>>[Cl:1][C:2]1[CH:11]=[C:10]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[C:9... | COc1ccc(COc2cc(Cl)nc3c(Cl)c(OC)ccc23)cc1 | COc1ccc2c(Cl)cc(Cl)nc2c1C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2-Chloro-8-methyl-7-methoxy-4-(4-methoxy-benzyloxy)-quinoline 221b was synthesized from compound 220b as a white powder in 50% yield, following the procedure as described for compound 221d. 1H NMR (CDCl3, 376 MHz) δ (ppm) 2.60 (s, 3H), 3.85 (s, 3H), 3.97 (s, 3H), 5.18 (s, 2H), 6.69 (s, 1H), 6.97 (d, J=8.57 Hz, 1H), 7.1... | COc1ccc(COc2cc(Cl)nc3c(C)c(OC)ccc23)cc1 | null | 50 | null |
1,289,304 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [CH2:1]([O:3][C:4](=[O:19])[NH:5][C@@H:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1)[CH2:7][NH2:8])[CH3:2].[CH:20](=O)[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1.[BH4-].[Na+]>CCO>[CH2:1]([O:3][C:4](=[O:19])[NH:5][C@@H:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16... | CCOC(=O)N[C@H](CN)c1cccc(C(F)(F)F)c1 | COc1ccc(C=O)cc1 | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 14 | Crude (S)-[2-amino-1-(3-trifluoromethyl-phenyl)-ethyl]-carbamic acid ethyl ester from above is dissolved in anhydrous EtOH (100 mL). p-Anisaldehyde (2.07 g, 15.2 mmol) is added into the solution and stirred at room temperature for 5 h before the addition of NaBH4 (0.82 g, 21.8 mmol) at 0° C. The mixture is then warmed ... | CCOC(=O)N[C@H](CNCc1ccc(OC)cc1)c1cccc(C(F)(F)F)c1 | null | null | null |
103,318 | ord_dataset-bdb961f26fac426eaa2de8f54a284acf | null | 1983-01-01T00:02:00 | true | [F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=[CH:18][C:13]=2[NH:12][C:11](=O)[C:10]([CH3:24])([CH3:23])[N:9]=1.[H-].[Na+].[C:27]([NH:30][NH2:31])(=O)[CH3:28]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([N+:19]([O-:21])=[O:20]... | CC1(C)N=C(c2ccccc2F)c2cc([N+](=O)[O-])ccc2NC1=O | CC(=O)NN | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 50 | 1 | 55.25 g (0.16 mol) of 5-(o-fluorophenyl)-1,3-dihydro-3,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one, dissolved in 800 ml of tetrahydrofuran, are treated portionwise and while stirring at room temperature with 9.7 g of a 55 to 60 percent sodium hydride dispersion and the mixture is stirred at 50° C. for a further 60 mi... | Cc1nnc2n1-c1ccc([N+](=O)[O-])cc1C(c1ccccc1F)=NC2(C)C | null | null | null |
1,756,334 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].C(=O)([O-])[O-].[K+].[K+].[CH3:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1.Cl>O1CCCC1.O>[CH3:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4])=[O:20])=[CH:17][CH:16]=1 | N[C@@H](CO)C(=O)O | Cc1ccc(C(=O)Cl)cc1 | null | Cl | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | 4 | 1 | L-Serine (100 g, 0.952 mol) (Wako Pure Chemical Industries, Ltd.), potassium carbonate (131.5 g, 0.952 mol) (Wako Pure Chemical Industries, Ltd.), and water 1 L were placed into a recovery flask (egg plant flask), followed by stirring vigorously. p-Methylbenzoyl chloride prepared in Step 1 was dissolved in tetrahydrofu... | Cc1ccc(C(=O)N[C@@H](CO)C(=O)O)cc1 | null | 64.7 | null |
327,241 | ord_dataset-b832171fa1674c469fbd33bc0ca1d5f1 | null | 1996-01-01T00:04:00 | true | [ClH:1].[CH2:2]([NH:10][C:11](=[O:25])[C@H:12]([C@H:21]([CH2:23][CH3:24])[CH3:22])[NH:13]C(OC(C)(C)C)=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CCCCCC>CCOC(C)=O>[ClH:1].[CH2:2]([NH:10][C:11](=[O:25])[C@H:12]([C@H:21]([CH2:23][CH3:24])[CH3:22])[NH2:13])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1 | CC[C@H](C)[C@H](NC(=O)OC(C)(C)C)C(=O)NCCc1ccccc1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CCCCCC | null | null | null | null | null | null | null | null | null | null | null | Hydrogen chloride gas was bubbled into a solution of N-t-butoxycarbonyl-L-isoleucine-phenethylamide (3.1 g, 9.3 mmol) in EtOAc (200 mL) at -20° C. in a dry ice-acetone bath until TLC (EtOAc: hexane, 1:3) indicated complete loss of starting material. The solution was concentrated to dryness to give 2.5 g (100%) of the t... | CC[C@H](C)[C@H](N)C(=O)NCCc1ccccc1 | null | 100 | null |
1,088,177 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH:13]1[CH:22]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[C:21](=O)[C:20]2[C:19]([C:31]([O:33]CC)=O)=[CH:18][CH:17]=[CH:16][C:15]=2[NH:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:37][NH2:38]>CO>[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH:13]1[NH:14][C:15... | NN | CCOC(=O)c1cccc2c1C(=O)C(c1ccc(F)cc1)C(c1nccn1Cc1ccccc1)N2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | 40 | 2 | A mixture of ethyl 2-(1-benzyl-1H-imidazol-2-yl)-3-(4-fluorophenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate (280 mg, 0.59 mmol) and hydrazine monohydrate (2 mL, 85%) in methanol (4 mL) was stirred at 40° C. for 2 hr, and then evaporated to half of the original volume. The mixture was filtrated and washed the so... | O=c1[nH]nc2c3c(cccc13)NC(c1nccn1Cc1ccccc1)C2c1ccc(F)cc1 | null | 96 | null |
722,023 | ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | null | 2006-01-01T00:08:00 | true | [NH2:1][CH:2]([C:5]1[C:6](=[O:16])[NH:7][C:8]([CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:9][N:10]=1)[CH2:3][CH3:4].[C:17]12([C:27](Cl)=[O:28])[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]3)[CH2:18]1)[CH2:24]2>>[CH:11]1([C:8]2[NH:7][C:6](=[O:16])[C:5]([CH:2]([NH:1][C:27]([C:17]34[CH2:26][CH:21]5[CH2:20][CH... | O=C(Cl)C12CC3CC(CC(C3)C1)C2 | CCC(N)c1nnc(C2CCCC2)[nH]c1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In analogy to the procedure for Example 36A, 150 mg (0.67 mmol) 6-(1-aminopropyl)-3-cyclopentyl-1,2,4-triazin-5(4H)-one, 150 mg (0.74 mmol) 1-adamantanecarbonyl chloride and proportionate amounts of the other reagents are used. The crude product is used in the next step without further purification. | CCC(NC(=O)C12CC3CC(CC(C3)C1)C2)c1nnc(C2CCCC2)[nH]c1=O | null | null | null |
288,400 | ord_dataset-96711be098434bc9ab567cb77fa3362b | null | 1994-01-01T00:04:00 | true | [CH2:1]([O:9][N:10]1[C:15]([CH3:17])([CH3:16])[CH2:14][CH:13]([N:18]([C:76]2[N:81]=[C:80](Cl)[N:79]=[C:78]([NH:83][CH2:84][CH2:85][CH2:86][CH2:87][CH:88]3[CH2:93][C:92]([CH3:95])([CH3:94])[N:91]([O:96][CH2:97][CH2:98][CH2:99][CH2:100][CH2:101][CH2:102][CH2:103][CH3:104])[C:90]([CH3:106])([CH3:105])[CH2:89]3)[N:77]=2)[C... | CCCCCCCCON1C(C)(C)CC(CCCCNc2nc(Cl)nc(N(CCCCCCN(c3nc(Cl)nc(NCCCCC4CC(C)(C)N(OCCCCCCCC)C(C)(C)C4)n3)C3CC(C)(C)N(OCCCCCCCC)C(C)(C)C3)C3CC(C)(C)N(OCCCCCCCC)C(C)(C)C3)n2)CC1(C)C | NCCCCCC(=O)[O-] | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound is prepared from the reaction of N,N'-bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-N,N'-bis{2-chloro-4-[N-(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-1,3,5-triazin-6-yl}-1,6-hexanediamine and sodium 6-aminohexanoate. | CCCCCCCCON1C(C)(C)CC(CCCCNc2nc(NCCCCCC(=O)O)nc(N(CCCCCCN(c3nc(NCCCCCC(=O)O)nc(NCCCCC4CC(C)(C)N(OCCCCCCCC)C(C)(C)C4)n3)C3CC(C)(C)N(OCCCCCCCC)C(C)(C)C3)C3CC(C)(C)N(OCCCCCCCC)C(C)(C)C3)n2)CC1(C)C | null | null | null |
1,132,068 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | [CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])[CH:3]=1.[Cl:19]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Cl:19][CH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[C:9](=[O:18])[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:16... | Cc1ccnc(N2C(=O)c3ccccc3C2=O)c1 | O=C1CCC(=O)N1Cl | null | O=C(OOC(=O)c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of 2-(4-methyl-pyridin-2-yl)-isoindole-1,3-dione (952 mg, 4 mmol)), N-chloro succinimide (640 mg, 4.8 mmol), and benzoyl peroxide (484 g, 2 mmol) in carbon tetrachloride (20 ml) was refluxed for 2 hr. After cooling to room temperature, the mixture was filtered and the filtrate was evaporated in vacuo. The res... | O=C1c2ccccc2C(=O)N1c1cc(CCl)ccn1 | null | 27.5 | null |
905,614 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [Li+].[OH-].[C:3]([O:7][C:8]([N:10]1[CH2:14][CH:13]([CH2:15][C:16]([O:18]C)=[O:17])[CH2:12][C@@H:11]1[C@H:20]1[O:24][C:23]([CH3:26])([CH3:25])[N:22]([C:27](=[O:29])[CH3:28])[C@H:21]1[CH2:30][C:31]1[CH:36]=[C:35]([F:37])[CH:34]=[C:33]([F:38])[CH:32]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>C1COCC1>[C:3]([O:7][C:8]([N:10]1[CH2... | COC(=O)CC1C[C@H]([C@H]2OC(C)(C)N(C(C)=O)[C@H]2Cc2cc(F)cc(F)c2)N(C(=O)OC(C)(C)C)C1 | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 8 | Add LiOH (0.32 mL, 3M solution in water) to a solution of (R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-methoxycarbonylmethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.1 g, 0.19 mmol) in 0.32 mL of THF and stir overnight. Remove THF under reduced pressure. Add ethyl acetate and... | CC(=O)N1[C@@H](Cc2cc(F)cc(F)c2)[C@@H]([C@H]2CC(CC(=O)O)CN2C(=O)OC(C)(C)C)OC1(C)C | null | 92.2 | null |
1,025,397 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | Br[C:2](Br)=[CH:3][C:4]1[C:9]([CH2:10][CH3:11])=[C:8]([O:12][CH3:13])[CH:7]=[CH:6][C:5]=1[CH2:14][CH3:15].[CH2:17]([NH2:20])[CH2:18][NH2:19]>>[CH2:10]([C:9]1[C:8]([O:12][CH3:13])=[CH:7][CH:6]=[C:5]([CH2:14][CH3:15])[C:4]=1[CH2:3][C:2]1[NH:19][CH2:18][CH2:17][N:20]=1)[CH3:11] | CCc1ccc(OC)c(CC)c1C=C(Br)Br | NCCN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2-(2,6-Diethyl-3-methoxy-benzyl)-4,5-dihydro-1H-imidazole was prepared from 2-(2,2-dibromo-vinyl)-1,3-diethyl-4-methoxy-benzene and ethylenediamine in analogy to Example 1e): yellow crystals; MS (ISP): 247.4 ([M+H]+, 100%). | CCc1ccc(OC)c(CC)c1CC1=NCCN1 | null | null | null |
1,442,919 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@@H:12]3[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]3)[N:9]=[C:10](I)[C:3]=12.[F:25][C:26]1[CH:41]=[CH:40][CH:39]=[CH:38][C:27]=1[O:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1... | OB(O)c1ccc(Oc2ccccc2F)cc1 | CC(C)(C)OC(=O)N1CCC[C@@H](n2nc(I)c3c(N)ncnc32)C1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | O | null | null | null | null | null | null | null | null | null | 100 | 8 | Into a 100 mL, 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of tert-butyl (3R)-3-[4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate (300 mg, 0.68 mmol, 1.00 equiv) in dioxane/H2O (7/3=V/V) (30 mL), [4-(2-fluorophenoxy)phenyl]boronic... | CC(C)(C)OC(=O)N1CCC[C@@H](n2nc(-c3ccc(Oc4ccccc4F)cc3)c3c(N)ncnc32)C1 | null | 58.3 | null |
1,284,293 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1OS(C1C=CC(C)=CC=1)(=O)=O)=[O:4].[CH:21]#[C:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>CCCCCCC.C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[C:21]#[C:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:4] | COC(=O)c1sccc1OS(=O)(=O)c1ccc(C)cc1 | C#CCCCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCCC | ClCCl | null | null | null | null | null | null | null | null | null | null | null | This product was prepared from 3-(toluene-4-sulfonyloxy)-thiophene-2-carboxylic acid methyl ester and 1-heptyne following the general procedure for the Sonogashira cross-coupling reaction described above. Chromatography eluent: heptane/DCM 1:1; yield (71 mg, 60%); 1H NMR δ (CDCl3): 7.32 (d, J=5.03 Hz, 1H), 7.01 (d, J=5... | CCCCCC#Cc1ccsc1C(=O)OC | null | null | null |
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