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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,289,829 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([C:11]3[CH2:12][CH2:13][CH2:14][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:16]=3)[N:6]2[N:5]=[CH:4][N:3]=1>C(O)(=O)C.[Pt](=O)=O>[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([CH:11]3[CH2:12][CH2:13][CH2:14][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[... | CC(C)(C)OC(=O)N1C=C(c2ccc3c(N)ncnn23)CCC1 | null | null | O=[Pt]=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | 64 | To a dry flask purged with N2 was added platinum (IV) oxide (150 mg, 0.66 mmol) followed by tert-butyl 5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydropyridine-1(2H)-carboxylate (2.09 mg, 6.63 mmol) as a solution in acetic acid (60 mL). The mixture was stirred under an H2 atmosphere for 64 h. The mixture was fi... | CC(C)(C)OC(=O)N1CCCC(c2ccc3c(N)ncnn23)C1 | null | 76 | null |
82,392 | ord_dataset-b1023e5ccd7142de9d250aa2e3e124db | null | 1981-01-01T00:06:00 | true | [O:1]=[C:2]1[C:9]2[C:5](=[C:6]([CH3:17])[N:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8]=2[CH3:10])[CH2:4][CH2:3]1.[BH4-].[Na+]>C(O)C>[OH:1][CH:2]1[C:9]2[C:5](=[C:6]([CH3:17])[N:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8]=2[CH3:10])[CH2:4][CH2:3]1 | Cc1c2c(c(C)n1-c1ccccc1)C(=O)CC2 | null | 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 | 0 | 8 | A solution of 1.5 g. (0.067 mole) of 4-oxo-1,3-dimethyl-2-phenyl-2,4,5,6-tetrahydrocyclopenta[c]pyrrole, described above in Example 10, and 254 mg. (0.0067 mole) of sodium borohydride in 15 ml. of ethanol was stirred for sixteen hours at 0°-5° C., then for an additional eight hours at ambient temperature and poured int... | Cc1c2c(c(C)n1-c1ccccc1)C(O)CC2 | null | null | null |
448,193 | ord_dataset-a4f0b79f6b9847168861270b79f84afa | null | 1999-01-01T00:11:00 | true | [N-:1]=[N+:2]=[N-:3].[Na+].[CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[S:15](Cl)(=[O:17])=[O:16]>O.CC(C)=O>[CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[S:15]([N:1]=[N+:2]=[N-:3])(=[O:16])=[O:17] | [N-]=[N+]=[N-] | O=S(=O)(Cl)c1ccc2ccccc2c1 | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(C)=O | null | null | null | null | null | null | null | null | null | null | 2 | A solution of sodium azide (3.1 g, 44 mmol) in water (10 ml) was added dropwise at RT to a stirred solution of 2-naphthalenesulfonyl chloride (10 g, 44 mmol) in acetone (60 ml) and stirring was continued for 2 hours. Water (50 ml) was added and the resulting mixture was decanted. The surnatant was discarded, while the ... | [N-]=[N+]=NS(=O)(=O)c1ccc2ccccc2c1 | null | 74.8 | null |
1,636,218 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([CH2:9][C:10]([O:12]C)=[O:11])[CH2:2]2>Cl>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([CH2:9][C:10]([OH:12])=[O:11])[CH2:2]2 | COC(=O)CC1CN2CCC1CC2 | null | 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 | 70 | 18 | A mixture of methyl 2-(quinuclidin-3-yl)acetate (1.1 g, 6.0 mmol) and 50 mL of conc. HCl [12M] was stirred at 70° C. for 18 h. The reaction mixture was concentrated under reduced pressure to afford crude 2-(quinuclidin-3-yl)acetic acid, which was used without purification in the next step (900 mg, 86%). | O=C(O)CC1CN2CCC1CC2 | null | null | null |
1,092,467 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | CS(C)=O.F[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]([CH3:15])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>O>[CH3:15][C:8]1[CH:7]=[C:6]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH:11]=[CH:10][C:9]=1[N+:12]([O-:14])=[O:13] | Cc1cc(F)ccc1[N+](=O)[O-] | C1COCCN1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | O | null | null | null | null | null | null | null | null | null | 80 | 18 | To a DMSO solution (8 ml) of 4-fluoro-2-methyl-1-nitro-benzene (500 mg), potassium carbonate (668 mg) and morpholine (0.42 ml) were added, followed by stirring at 80° C. for 18 hours. This was cooled to room temperature, and water (30 ml) was added, followed by extraction with ethyl acetate (50 ml×2). The organic layer... | Cc1cc(N2CCOCC2)ccc1[N+](=O)[O-] | null | 95 | null |
822,727 | ord_dataset-ec58fad8331a42c5a67ad75aac6713b4 | null | 2008-01-01T00:05:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[C:11]([NH:15][NH2:16])[N:12]=[N:13][CH:14]=2)=[CH:5][CH:4]=1.[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[N:13][N:12]3[C:23](=[O:24])[NH:16][N:15]=[C:11]3[C:10]=2[C:17]2[CH:22]=[... | COc1ccc(-c2cnnc(NN)c2-c2ccncc2)cc1 | O=C(n1ccnc1)n1ccnc1 | 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 by reacting 1-(5-(4-methoxyphenyl)-4-(pyridin-4-yl)pyridazin-3-yl)hydrazine with carbonyldiimidazole (CDI) by procedures analogous to those described in Example 279F to give 7-(4-methoxyphenyl)-8-(pyridine-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one. LC/MS (method A): RT=1.37 min, (M... | COc1ccc(-c2cnn3c(=O)[nH]nc3c2-c2ccncc2)cc1 | null | null | null |
821,701 | ord_dataset-ec58fad8331a42c5a67ad75aac6713b4 | null | 2008-01-01T00:05:00 | true | [CH2:1]([P:8]([CH2:11][CH:12]([CH2:18][C:19]1[CH:20]=[N:21][C:22]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:23][CH:24]=1)[C:13]([O:15]CC)=[O:14])(=[O:10])[OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-]>C1COCC1.O>[CH2:1]([P:8]([CH2:11][CH:12]([CH2:18][C:19]1[CH:20]=[N:21][C:22]([NH:... | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)CP(=O)(O)Cc1ccccc1 | 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 | 25 | 8 | Benzyl[2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-3-ethoxy-3-oxopropyl]phosphinic acid (62 mg; 0.13 mmol) was dissolved in THF (1 mL) and water (1 mL). LiOH (12 mg; 0.5 mmol) was added, and the reaction was stirred at room temperature overnight. The reaction mixture was concentrated, water (1 mL) was added ... | CC(C)(C)OC(=O)Nc1ccc(CC(CP(=O)(O)Cc2ccccc2)C(=O)O)cn1 | null | 81.5 | null |
1,729,813 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[N:5]=[C:4]([NH:12][CH2:13][CH2:14][CH3:15])[N:3]=1.Cl.Cl.[CH3:18][NH:19][NH:20][CH3:21].[OH-].[Na+]>O1CCOCC1.O>[CH2:13]([NH:12][C:4]1[N:5]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[N:7]=[C:2]([N:19]([CH3:18])[NH:20][CH3:21])[N:3]=1)[CH2:14][CH3:15] | CCCNc1nc(Cl)nc(NCCC)n1 | CNNC | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1COCCO1 | null | null | null | null | null | null | null | null | null | 60 | null | A mixture of 2-chloro-N-(4,6-bis-(n-propylamino)-[1,3,5]triazine (XXXIV) (2.50 g, 10.88 mmol), N,N′-dimethyl-hydrazine dihydrochloride (2.89 g, 21.76 mmol) and NaOH (2.18 g, 54.40 mmol) in 1,4-dioxane (40 mL) and water (20 mL) was heated at 60° C. for 18 h. The volatiles were removed under reduced pressure. Saturated N... | CCCNc1nc(NCCC)nc(N(C)NC)n1 | null | 42.4 | null |
1,256,869 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | [C:1]([O:5][C:6](=[O:26])[NH:7][CH:8]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=1)[C:9]([C:11]1[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=1)=[O:10])([CH3:4])([CH3:3])[CH3:2].[NH2:27][C:28]([C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=1)=[O:29]>>[C:1]([O:5][C:6](=[O:26])[NH:7][CH:8]([C:18]1[CH:23]=... | NC(=O)c1cccc(B(O)O)c1 | CC(C)(C)OC(=O)NC(C(=O)c1ccc(I)cc1)c1ccc(Cl)c(Cl)c1 | 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 from rac-[1-(3,4-dichloro-phenyl)-2-(4-iodo-phenyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester and 3-aminocarbonylphenyl-boronic acid in analogy to Example 2b): MS (ISN): 497.2 and 499.2 (M−H)−. | CC(C)(C)OC(=O)NC(C(=O)c1ccc(-c2cccc(C(N)=O)c2)cc1)c1ccc(Cl)c(Cl)c1 | null | null | null |
207,855 | ord_dataset-ac1c7aa04d6c4e588e723e3e05721681 | null | 1990-01-01T00:05:00 | true | C([NH:4][C:5](=[CH:9][CH2:10][PH:11]([CH2:13]O)=[O:12])[C:6]([OH:8])=[O:7])(=O)C.[ClH:15].C[OH:17]>>[ClH:15].[ClH:15].[NH2:4][C@H:5]([C:6]([OH:8])=[O:7])[CH2:9][CH2:10][P:11]([CH3:13])(=[O:17])[OH:12] | CC(=O)NC(=CC[PH](=O)CO)C(=O)O | CO | 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 | 0.0087 g (0.019 mmol) of chloronorbornadienerhodium(I) dimer and 0.022 g (0.053 mmol) of the compound Va are dissolved in 5 ml of methanol under an atmosphere of argon. The catalyst solution obtained is added under argon to a solution of 2.21 g (0.01 mol) of 2-acetamido-4-(hydroxymethylphosphinyl)-2-butenoic acid in 45... | CP(=O)(O)CC[C@H](N)C(=O)O | null | 91.9 | null |
774,049 | ord_dataset-8214eb8444a44dc2900ccb42dbeff15e | null | 2007-01-01T00:05:00 | true | [OH-].[Na+].C([O:10][C:11](=[O:34])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:14][C:13]=1[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)C1C=CC=CC=1.Cl>CO>[CH2:27]([O:26][C:13]1[CH:14]=[C:15]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C... | O=C(OCc1ccccc1)c1ccc(OCc2ccccc2)cc1OCc1ccccc1 | null | null | Cl | [Na+] | [OH-] | 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 | 65 | 48 | NaOH (1 N) (150 mL) was added to compound 36 (4.3 g) in MeOH (50 mL). The reaction mixture was heated to 65° C. with stirring for 48 h. After the reaction mixture was cooled down to room temperature, 1.0 M HCl (200 mL) was added to neutralize the reaction mixture. The solvent was concentrated under reduced pressure. Th... | O=C(O)c1ccc(OCc2ccccc2)cc1OCc1ccccc1 | null | 38.4 | null |
1,763,236 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:23]#[N:24])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:20][CH3:21])[C:17](O)=[O:18])[C:10](=[O:22])[CH:9]=2)[CH:7]=1.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[N:36]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[NH:35][C:34](=[O:44])[CH:33]=2)=[CH:28][CH... | CC(C)(C)OC(=O)n1[nH]c(=O)cc1-c1ccc(N)cc1 | CCC(C(=O)O)n1cc(OC)c(-c2cc(Cl)ccc2C#N)cc1=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 | 87 mg (0.25 mmol) of 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoic acid (racemate) and 84 mg (purity 90%, 0.28 mmol, 1.1 eq.) of tert-butyl 5-(4-aminophenyl)-3-oxo-2,3-dihydro-1H-pyrazole-1-carboxylate were reacted according to General Method 5A. The crude product was purified by preparative HP... | CCC(C(=O)Nc1ccc(-c2cc(=O)[nH]n2C(=O)OC(C)(C)C)cc1)n1cc(OC)c(-c2cc(Cl)ccc2C#N)cc1=O | null | null | null |
1,424,063 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [CH2:1]([N:3]1[CH2:8][CH2:7][CH2:6][C@@H:5]([CH2:9][N:10]2[CH2:15][CH2:14][N:13](C(OCC3C=CC=CC=3)=O)[CH2:12][CH2:11]2)[CH2:4]1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([N:3]1[CH2:8][CH2:7][CH2:6][C@@H:5]([CH2:9][N:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)[CH2:4]1)[CH3:2] | CCN1CCC[C@@H](CN2CCN(C(=O)OCc3ccccc3)CC2)C1 | null | null | [Pd] | 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 | 25 | 18 | Benzyl 4-{[(3R)-1-ethylpiperidin-3-yl]methyl}piperazine-1-carboxylate (352 mg) was dissolved in ethanol (50 ml). 10% Palladium on carbon (35 mg) was added and the mixture stirred for 18 hours at room temperature under an atmosphere of hydrogen. The reaction mixture was filtered through a pad of celite and the filtrate ... | CCN1CCC[C@@H](CN2CCNCC2)C1 | null | 104.5 | null |
1,229,777 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:19][CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[C:13](N(OC)C)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[CH:26]([Mg]Br)=[CH2:27].Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:19][CH:20]2[CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)[C:13](=[O:14])[CH:26]=[CH2:27])[... | CON(C)C(=O)C(CC1CCOCC1)c1ccc(S(C)(=O)=O)c(Cl)c1 | C=C[Mg]Br | null | Cl | 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 | 3 | A solution of 2-[3-chloro-4-(methylsulfonyl)phenyl]-N-methoxy-N-methyl-3-(tetrahydro-2H-pyran-4-yl)propanamide (8.64 g) in tetrahydrofuran (90 mL) was cooled to 0° C., and vinylmagnesium bromide (1.0M tetrahydrofuran solution, 88.8 mL) was added dropwise. The reaction mixture was stirred at room temperature for 3 hr, a... | C=CC(=O)C(CC1CCOCC1)c1ccc(S(C)(=O)=O)c(Cl)c1 | null | 90 | null |
361,092 | ord_dataset-0b24d1f58a024ed7bc2bda95b2430c72 | null | 1997-01-01T00:04:00 | true | [CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[C:11]([CH3:13])[C:10]([OH:14])=[C:9]([CH3:15])[CH:8]=2)[N:3]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26]O)=[CH:20][N:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C(Cl)Cl>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:2... | COc1ccc(CCCO)cn1 | Cc1nc(-c2cc(C)c(O)c(C)c2)no1 | null | CCOC(=O)/N=N/C(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 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 | To a suspension of 0.81 g (3.9 mmol) of 4-(5-methyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenol, 0.8 g (1.2 eq) of 2-methoxy-5-(3-hydroxypropyl)-pyridine, 1.4 g (1.2 eq) of triphenylphosphine in 70 ml of methylene chloride under nitrogen at 5° C. was added in portions 0.88 g (1.2 eq) of DEAD. The mixture was concentrated ... | COc1ccc(CCCOc2c(C)cc(-c3noc(C)n3)cc2C)cn1 | null | 72.6 | null |
74,229 | ord_dataset-b9d8ddf9c2884d40859b6b5f24815a7d | null | 1980-01-01T00:12:00 | true | [Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([C:8]2[C:24]([CH3:25])=[CH:23][C:11]([O:12][CH2:13][CH2:14][CH2:15][C:16]([CH3:22])([CH3:21])[C:17]([O:19]C)=[O:18])=[CH:10][C:9]=2[CH3:26])=[O:7])=[CH:4][CH:3]=1>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[C:9]([CH3:26])=[CH:10][C:11]([O:12][CH2:13][CH2:14][CH2:15][C:16]([CH3:... | COC(=O)C(C)(C)CCCOc1cc(C)c(C(=O)c2ccc(Cl)cc2)c(C)c1 | null | 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 | null | null | The ester of Example 3 is saponified with methanol containing soda to give the desired acid, m.pt 135° C. | Cc1cc(OCCCC(C)(C)C(=O)O)cc(C)c1C(=O)c1ccc(Cl)cc1 | null | null | null |
12,876 | ord_dataset-a0071d97083e4e69ae8872417ed2776b | null | 1976-01-01T00:09:00 | true | [CH:1]1([C:6]2([CH3:12])[CH2:10][CH2:9][CH2:8][C:7]2=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.BrBr.S(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH:1]1([C:6]2([CH3:12])[C:7](=[O:11])[CH:8]=[CH:9][CH2:10]2)[CH2:5][CH2:4][CH2:3][CH2:2]1 | CC1(C2CCCC2)CCCC1=O | null | null | BrBr | O=S([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | Four grams (0.026 mole) of 2-cyclopentyl-2-methyl-cyclopentanone dissolved in 20 ml. of chloroform is cooled to 0°C. and 4.2 g. (0.026 mole) of bromine is added over a 40 minute interval. An aqueous 5 wt. % solution of sodium bisulfite is added to destroy the excess bromine followed by 10 wt. % aqueous sodium hydroxide... | CC1(C2CCCC2)CC=CC1=O | null | null | null |
1,729,346 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [CH2:1]([C@@H:8]([CH2:12][CH2:13][C@H:14]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:15]([NH:17][C@H:18]1[CH2:24][CH2:23][S:22][C@H:21]2[CH2:25][CH2:26][CH2:27][C@@H:28]([C:29]([O:31][CH3:32])=[O:30])[N:20]2[C:19]1=[O:33])=[O:16])[C:9](O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:41][C@@H:42]1... | N[C@H]1CNC(=O)[C@H]2CCCCN2C1=O | COC(=O)[C@@H]1CCC[C@@H]2SCC[C@H](NC(=O)[C@H](CC[C@H](Cc3ccccc3)C(=O)O)Cc3ccccc3)C(=O)N21 | 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 | (4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-((4R,10aR)-1,5-dioxodecahydropyrido[1,2-a][1,4]diazepin-4-ylamino)-6-oxohexanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate was synthesized as described in General Procedure H using Intermediate 23 (20 mg, 0.035 mmol) and Intermediate 39 (7.0 mg, 0.035 ... | COC(=O)[C@@H]1CCC[C@@H]2SCC[C@H](NC(=O)[C@H](CC[C@H](Cc3ccccc3)C(=O)N[C@@H]3CNC(=O)[C@H]4CCCCN4C3=O)Cc3ccccc3)C(=O)N21 | null | null | null |
981,429 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:6].C([O-])([O-])=O.[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O>[CH2:17]([O:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[OH:1])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1 | BrCc1ccccc1 | N#Cc1ccc(O)c(O)c1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | 72 | A mixture of 3,4-dihydroxybenzonitrile (540 mg, 4 mmol), K2CO3 (552 mg, 4 mmol) and benzyl bromide (476 mg, 4 mmol) in acetone (20 mL) was stirred at room temperature for 3 days. The mixture was evaporated under vacuum and subjected to flash column chromatography (2% MeOH in toluene-hexane, 2:1) to give the desired pro... | N#Cc1ccc(OCc2ccccc2)c(O)c1 | null | 24.9 | null |
385,839 | ord_dataset-d330662edaed408d950898172aba7a4c | null | 1997-01-01T00:12:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:14]I>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8] | CI | O=C(O)C=Cc1ccc(Cl)c(Cl)c1 | 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 | null | 0.25 | 1: Cool a solution of 3-(3,4-dichlorophenyl)-2-propeneoic acid (100 g, 461 mmol) in dry DMF (500 mL) to 0° C. and treat with Cs2 CO3 (100 g, 307 mmol, 0.66 eq). Stir the resulting off-white slurry for 15 min, then add CH3I (33 mL, 530 mmol, 1.15 eq) via syringe. After 1 h, add additional DMF (250 mL), stir the slurry f... | COC(=O)C=Cc1ccc(Cl)c(Cl)c1 | null | 98.9 | null |
1,017,444 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | C([O:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[N:18]([CH3:19])[C:17]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[C:11]=1[NH:20][C:21]1[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=1[F:28])=[O:9])=C.Cl.C(=O)([O-])O.[Na+]>CO>[OH:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[N:18]([CH3:19])[C:17]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[C... | C=COCCONC(=O)c1c(Nc2ccc(I)cc2F)c2cnccc2n1C | null | null | Cl | O=C([O-])O | [Na+] | 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 | 25 | 20 | A mixture of 3-(2-fluoro-4-iodo-phenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid (2-vinyloxy-ethoxy)-amide (64 mg, 0.13 mmol), 1N aqueous HCl (0.39 mL) and MeOH (4.0 ml) was stirred at room temperature for 20 hours. Sodium hydrogen carbonate (32 mg, 0.39 mmol) was added, stirring was continued for 10 m... | Cn1c(C(=O)NOCCO)c(Nc2ccc(I)cc2F)c2cnccc21 | null | 26.2 | null |
1,746,448 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[O:11][C:10]([C:12]3[C:13]([NH2:25])=[N:14][CH:15]=[C:16]([C:18]4[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=4)[CH:17]=3)=[N:9][N:8]=2)[CH2:3][CH2:2]1.[H-].[Na+].[CH3:28]I>C1COCC1>[CH3:28][N:1]1[CH2:6][CH2:5][CH:4]([C:7]2[O:11][C:10]([C:12]3[C:13]([NH2:25])=[N:14][CH:15]=[C:16]([C:1... | CI | Cc1ccc(-c2cnc(N)c(-c3nnc(C4CCNCC4)o3)c2)cc1 | 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 | 0 | 1 | To a solution of 3-(5-piperidin-4-yl-[1,3,4]oxadiazol-2-yl)-5-p-tolyl-pyridin-2-ylamine (250 mg, 0.746 mmol) in THF (25 mL) was added NaH (55%) (48.8 mg, 1.119 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 1 h. Then MeI (95 mg, 0.671 mmol) was added at 0° C., and the reaction mixture was stirred at 0° C.... | Cc1ccc(-c2cnc(N)c(-c3nnc(C4CCN(C)CC4)o3)c2)cc1 | null | null | null |
1,641,843 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | C([O:3][C:4](=[O:32])[CH2:5][C@@H:6]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH2:19][C:20]2[C:28]3[S:27][C:26](=[O:29])[NH:25][C:24]=3[CH:23]=[C:22]([Br:30])[CH:21]=2)[C:11]1=[O:31])[CH2:7][CH2:8][CH3:9])C.[Li+].[OH-].Cl>O1CCOCC1.O>[Br:30][C:22]1[CH:21]=[C:20]([CH2:19][N:12]2[C:13]3[CH:18]=[CH:17][C... | CCC[C@@H](CC(=O)OCC)n1c(=O)n(Cc2cc(Br)cc3[nH]c(=O)sc23)c2ccccc21 | null | null | Cl | [Li+] | [OH-] | 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 | null | 1 | (S)-3-[3-(5-Bromo-2-oxo-2,3-dihydro-benzothiazol-7-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl ester (33 mg, 0.06 mmol) is dissolved in dioxane (3 mL) and then LiOH (8 mg, 0.3 mmol) in water (3 mL) is added to the reaction. The reaction is stirred for 1 hour then acidified with 4N HCl and the sol... | CCC[C@@H](CC(=O)O)n1c(=O)n(Cc2cc(Br)cc3[nH]c(=O)sc23)c2ccccc21 | null | 34 | null |
481,975 | ord_dataset-21c1b1c06c7e4e09a38b5b1c71a32e52 | null | 2000-01-01T00:10:00 | true | [CH2:1]([OH:4])[CH2:2][OH:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:16]([O:18][C:19]([CH2:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][C:23]1=O)=[O:20])[CH3:17]>C1(C)C=CC=CC=1>[CH2:16]([O:18][C:19]([CH2:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][C:23]21[O:4][CH2:1][CH2:2][O:3]2)=[O:20])[CH3:17] | CCOC(=O)CC1CCCCC1=O | OCCO | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 25 | null | Under an argon atmosphere, ethylene glycol (7.6 ml, 135.87 mmol) and para-toluenesulfonic acid (516 mg, 2.72 mmol) were added to a solution of (±)-2-(ethoxycarbonylmethyl)cyclohexanone (5.00 g, 27.17 mmol) in toluene (136 ml). The mixture was heated to reflux in a Dean Stark apparatus for 4 h and then allowed to cool t... | CCOC(=O)CC1CCCCC12OCCO2 | null | 74 | null |
1,732,265 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [OH-].[Na+].[Br:3][C:4]1[C:12]2[S:11][C:10]([C:13]([O:15]C)=[O:14])=[CH:9][C:8]=2[CH:7]=[C:6]([C:17]([F:20])([F:19])[F:18])[CH:5]=1>O1CCOCC1>[Br:3][C:4]1[C:12]2[S:11][C:10]([C:13]([OH:15])=[O:14])=[CH:9][C:8]=2[CH:7]=[C:6]([C:17]([F:20])([F:18])[F:19])[CH:5]=1 | COC(=O)c1cc2cc(C(F)(F)F)cc(Br)c2s1 | null | null | [Na+] | [OH-] | 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 | 70 | null | A solution of NaOH (4.0 M in water, 5.0 mL, 20 mmol) was added to a solution of methyl 7-bromo-5-(trifluoromethyl)-1-benzothiophene-2-carboxylate (1.00 g, 2.95 mmol) in dioxane (11 mL). The mixture was heated at 70° C. overnight, allowed to cool to room temperature, then concentrated. The resulting light beige solid wa... | O=C(O)c1cc2cc(C(F)(F)F)cc(Br)c2s1 | null | null | null |
619,909 | ord_dataset-2952e63264f5422a84e12cca1e0541ee | null | 2003-01-01T00:12:00 | true | [Cl:1][C:2]1[CH:15]=[C:14]([F:16])[C:13]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]([CH3:28])[C:18]2=[O:29])=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:37]([CH3:43])[C:38]([O:40][CH2:41][CH3:42])=[O:39]>CN(C)C=O>[Cl:1][C:2]1[CH:15]=... | CCOC(=O)C(C)Br | Cn1c(C(F)(F)F)cc(=O)n(-c2cc(Oc3ccc(O)cc3)c(Cl)cc2F)c1=O | 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 | null | 100 mg of 4-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}phenol (produced in Intermediate Production Example 1) was dissolved in 1.0 ml of N,N-dimethylformamide, and to this was added 42 mg of anhydrous potassium carbonate, and 46 mg of ethyl 2-bromopropionate wa... | CCOC(=O)C(C)Oc1ccc(Oc2cc(-n3c(=O)cc(C(F)(F)F)n(C)c3=O)c(F)cc2Cl)cc1 | null | 69 | null |
1,285,492 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [CH2:1]([S:8][C:9]1[S:13][C:12]([SH:14])=[N:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:18]1[C:19]([C:24]#[N:25])=[N:20][CH:21]=[CH:22][N:23]=1>CN(C=O)C.C1C=CC=CC=1>[CH2:1]([S:8][C:9]1[S:13][C:12]([S:14][C:18]2[C:19]([C:24]#[N:25])=[N:20][CH:21]=[CH:22][N:23]=2)=[N:11][N:10]=1)[C:2]1[CH:3]=[CH:... | N#Cc1nccnc1Cl | Sc1nnc(SCc2ccccc2)s1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | CN(C)C=O | null | null | null | null | null | null | null | null | null | 0 | 0.25 | To a solution of 5-(benzylthio)-1,3,4-thiadiazole-2-thiol (240 mg, 1.00 mmol) in DMF and benzene (4 ml, 1/1) was added NaH (60% dispersion in mineral oil, 44 mg, 1.10 mmol) slowly at 0° C. under a nitrogen atmosphere. The resulting suspension was stirred at 0° C. for 15 minutes and then to the mixture was added 3-chlor... | N#Cc1nccnc1Sc1nnc(SCc2ccccc2)s1 | null | null | null |
740,118 | ord_dataset-437aa6654d5044ddaef3346dc4c6e08a | null | 2006-01-01T00:11:00 | true | [C:1]([C:3]1[CH:4]=[C:5]([C:16](=[O:25])[C:17]2[CH:22]=[CH:21][C:20]([CH2:23]Br)=[CH:19][CH:18]=2)[N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][C:7]=12)#[N:2].C(C1C=[C:30](C(=O)C2C=CC(C)=CC=2)[N:31]2C3C(=CC=CC=3)C=C[C:32]=12)#N>>[C:1]([C:3]1[CH:4]=[C:5]([C:16](=[O:25])[C:17]2[CH:22]=[CH:21][C:20]([... | Cc1ccc(C(=O)c2cc(C#N)c3ccc4ccccc4n23)cc1 | N#Cc1cc(C(=O)c2ccc(CBr)cc2)n2c1ccc1ccccc12 | 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 | 3-Cyano-1-[4-(bromomethyl)benzoyl]-pyrrolo[1,2-a]quinoline. The title compound was prepared similar as Example 53a, using 3-cyano-1-(4-methylbenzoyl)-pyrrolo[1,2-a]quinoline to yield 230 mg (68%). 1H NMR (CDCl3): 8.09–8.10 (m, 3H), 7.87–7.52 (m, 7H), 7.43 (s, 1H), 4.58 (s, 2H). | CN(C)Cc1ccc(C(=O)c2cc(C#N)c3ccc4ccccc4n23)cc1 | null | null | null |
95,671 | ord_dataset-6f715747ea754945a2f0af4a8482c7d2 | null | 1982-01-01T00:06:00 | true | [NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]([Cl:10])([Cl:9])[Cl:8])[N:3]=1.[Cl:11][C:12]([Cl:17])([Cl:16])[C:13](Cl)=[O:14]>C1(C)C(C)=CC=CC=1>[Cl:11][C:12]([Cl:17])([Cl:16])[C:13]([NH:1][C:2]1[S:6][N:5]=[C:4]([C:7]([Cl:10])([Cl:9])[Cl:8])[N:3]=1)=[O:14] | O=C(Cl)C(Cl)(Cl)Cl | Nc1nc(C(Cl)(Cl)Cl)ns1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1C | null | null | null | null | null | null | null | null | null | null | 120 | null | To a solution of 10.9 grams (0.05 mole) 5-amino-3-trichloromethyl-1,2,4-thiadiazole in 200 milliliters xylene at 110° C. was added 18.2 grams (0.1 mole) trichloroacetyl chloride over 0.5 hour. After heating for an additional 20 hours at 120° C., the low boiling materials were distilled in vacuo to leave 15.8 grams (87%... | O=C(Nc1nc(C(Cl)(Cl)Cl)ns1)C(Cl)(Cl)Cl | null | 86.8 | null |
1,258,651 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | [F:1][C:2]([F:27])([F:26])[C:3](O)([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=1)[CH2:4][C:5]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)=[N:6][OH:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C(OC)(C)(C)C>[CH3:14][C:11]1[CH:10]=[CH:9][C:8]([C:5]2[CH2:4... | Cc1ccc(C(CC(O)(c2cccc(C(F)(F)F)c2)C(F)(F)F)=NO)cc1 | null | null | CCOC(=O)N=NC(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COC(C)(C)C | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 24 | To a solution of 4,4,4-trifluoro-3-hydroxy-1-(4-methylphenyl)-3-[3-(trifluoromethyl)phenyl]butan-1-one oxime (0.45 g) and triphenylphosphine (0.60 g) in tetrahydrofuran (10 mL), diethyl azodicarboxilate (0.44 g) was added, and the mixture was stirred for 24 hours at room temperature. After the reaction solution was dil... | Cc1ccc(C2=NOC(c3cccc(C(F)(F)F)c3)(C(F)(F)F)C2)cc1 | null | 25.6 | null |
1,740,960 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | Cl.[CH:2]1([CH2:5][O:6][C:7]2[CH:12]=[C:11]([O:13][CH3:14])[C:10]([F:15])=[CH:9][C:8]=2[C:16]2[C:17]3[NH:24][C:23]([CH3:25])=[C:22]([C:26]([NH:28][C@@H:29]4[CH2:34][CH2:33][NH:32][CH2:31][C@H:30]4[OH:35])=[O:27])[C:18]=3[N:19]=[CH:20][N:21]=2)[CH2:4][CH2:3]1.[C:36](Cl)(=[O:38])[CH3:37]>>[C:36]([N:32]1[CH2:33][CH2:34][C... | CC(=O)Cl | COc1cc(OCC2CC2)c(-c2ncnc3c(C(=O)N[C@@H]4CCNC[C@H]4O)c(C)[nH]c23)cc1F | 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 | Starting from 4-[2-(cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-N-[(3R*,4R*)-3-hydroxypiperidin-4-yl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide hydrochloride (example D.f47) and commercially available acetyl chloride the title compound is obtained as colorless solid. | COc1cc(OCC2CC2)c(-c2ncnc3c(C(=O)N[C@@H]4CCN(C(C)=O)C[C@H]4O)c(C)[nH]c23)cc1F | null | null | null |
348,355 | ord_dataset-66f304805e5d47fc8d3c722b1bd8dfa2 | null | 1996-01-01T00:12:00 | true | C[C:2]1(C)[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])O1.N1C=CC=CC=1.[C:17]1([CH2:23]C(Cl)=O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>C(Cl)Cl>[C:17]1([CH2:23][C:4](=[O:5])[CH2:6][C:7]([O:9][CH3:2])=[O:8])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1 | O=C(Cl)Cc1ccccc1 | CC1(C)OC(=O)CC(=O)O1 | null | Cl | 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 | 0 | null | In 70 ml of methylene chloride was dissolved 36.03 g (0.25 mol) of Meldrum's acid. Pyridine (38.17 g, 0.48 mol) was used as a base. To the solution was added dropwise 42.52 g (0.275 mol) of phenylacetyl chloride in an ice bath while stirring. After the reaction, ice-water and diluted hydrochloric acid were added to was... | COC(=O)CC(=O)Cc1ccccc1 | null | 91.6 | null |
1,654,105 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [CH3:1][O:2][P:3]([CH2:7][C:8](=[O:20])[CH:9]([CH3:19])[CH2:10][C:11]#[C:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:6])[O:4][CH3:5]>[Pd].CO>[CH3:1][O:2][P:3]([CH2:7][C:8](=[O:20])[CH:9]([CH3:19])[CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)(=[O:6])[O:4][CH3:5] | COP(=O)(CC(=O)C(C)CC#Cc1ccccc1)OC | null | null | [Pd] | 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 | null | 8 | A mixture consisting of (±)-dimethyl(3-methyl-2-oxo-6-phenylhex-5-yn-1-yl)phosphonate (15db(i)/15dc(i)), (1.0 g, 3.4 mmol) and 10% palladium on activated carbon (15 mg) in methanol (30 mL) was stirred under an atmosphere of hydrogen overnight. The hydrogen was evacuated and the mixture was filtered through a micropore ... | COP(=O)(CC(=O)C(C)CCCc1ccccc1)OC | null | 98.6 | null |
376,204 | ord_dataset-846d411edee44814931e062174d7ef12 | null | 1997-01-01T00:09:00 | true | [Li].[C:2]([O:5][C:6]1[C:7]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:8][C:9]([OH:18])=[C:10]([C:13]=1[C:14]([CH3:17])([CH3:16])[CH3:15])[CH:11]=[O:12])(=[O:4])[CH3:3].Br[CH:24]([CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28].[Cl-].[NH4+]>O1CCCC1>[C:2]([O:5][C:6]1[C:7]([C:19]([CH3:22])... | CC(=O)Oc1c(C(C)(C)C)cc(O)c(C=O)c1C(C)(C)C | CC(C)CCC(Br)CCC(C)C | null | [Cl-] | [Li] | [NH4+] | 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 | 0 | 8 | Lithium (2.8 g) was added to a solution of 5-acetoxy-4,6-di-tert-butyl-2-hydroxybenzaldehyde (24.3 g) and 5-bromo-2,8-dimethylnonane (47.0 g) in tetrahydrofuran (200 ml) under ice cooling under a nitrogen atmosphere and the mixture was stirred overnight. The reaction mixture was poured into ice water, neutralized with ... | CC(=O)Oc1c(C(C)(C)C)cc(O)c(C(O)C(CCC(C)C)CCC(C)C)c1C(C)(C)C | null | 45.6 | null |
116,378 | ord_dataset-19041548671f410397ce7f00536a9be3 | null | 1984-01-01T00:04:00 | true | [CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[C:5](=[O:16])[C:4]([CH2:17][S:18][CH3:19])=[CH:3]1.ClC1C=CC=C(C(OO)=[O:28])C=1>ClCCl>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:14])([F:15])[F:13])[CH:10]=2)[C:5](=[O:16])[C:4]([CH2:17][S:18]([CH3:19])=[O:28])=[CH:3]1 | O=C(OO)c1cccc(Cl)c1 | CSCc1cn(C)c2cc(C(F)(F)F)ccc2c1=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 | null | To a stirred solution of 1-methyl-3-methylthiomethyl-7-trifluoromethyl-4-quinolone (6.5 g.) in dichloromethane (150 ml.) at -10° was added a solution of 3-chloroperbenzoic acid (85%, 4.2 g.) in dichloromethane (90 ml.) during 30 minutes. The solution was extracted with saturated aqueous sodium bicarbonate until free of... | Cn1cc(CS(C)=O)c(=O)c2ccc(C(F)(F)F)cc21 | null | null | null |
1,401,783 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[O:22][N:21]=[C:20]([CH3:23])[C:19]=3[NH2:24])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)[CH3:2].Br[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:28]=1>>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]... | Brc1cccc(-c2ccccc2)n1 | CCOC(=O)Cc1ccc(-c2ccc(-c3onc(C)c3N)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 | Prepared according to the procedure described in Example 68, Step 2, using [4′-(4-amino-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-acetic acid ethyl ester and 2-bromo-6-phenyl-pyridine. | CCOC(=O)Cc1ccc(-c2ccc(-c3onc(C)c3Nc3cccc(-c4ccccc4)n3)cc2)cc1 | null | null | null |
278,863 | ord_dataset-140fb5527ff24f97bcf0094c5d100120 | null | 1993-01-01T00:11:00 | true | C(O[C:4](=[O:22])[CH:5]([N:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:16](=[O:21])C(Cl)(Cl)Cl)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.Cl.[Br:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[C:27]([F:33])[CH:26]=1.C(N(CC)CC)C.Cl>CN(C)C=O>[CH2:9]([O:8][C:6]([CH:5]1[N:11]2[CH:15]=[CH:14][CH:13]=[C:12]2[C:16](=[O:21])[N:30]([CH2:2... | NCc1ccc(Br)cc1F | CCOC(=O)C(C(=O)OCC)n1cccc1C(=O)C(Cl)(Cl)Cl | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CN(C)C=O | null | null | null | null | null | null | null | null | null | 70 | 1 | A mixture of 2-(2-trichloroacetylpyrrol-1-yl)malonic acid diethyl ester (40.0 g), 4-bromo-2-fluorobenzylamine hydrochloride (29.0 g) and triethylamine (54.8 g, 75.0 ml) in anhydrous dimethylformamide (100 ml) was stirred under the stream of nitrogen at 70° C. for 1 hour. After cooling, the reaction mixture was poured i... | CCOC(=O)C1C(=O)N(Cc2ccc(Br)cc2F)C(=O)c2cccn21 | null | 86 | null |
586,657 | ord_dataset-cb5dd7a8b94e4f19a9148a1904b0dcb6 | null | 2003-01-01T00:03:00 | true | C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[C:19]([O:21][Si:22]([C:35]([CH3:38])([CH3:37])[CH3:36])([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:18]=[CH:17][C:16]=2[F:39])[C:10](=[O:40])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:39... | CC(C)(C)OC(=O)N1CCN(Cc2cc(O[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)ccc2F)C(=O)C1 | null | null | O=C([O-])O | [Na+] | 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 | null | 2 | To a solution of product from Step E (2.1 g, 3.74 mmol) in methylene chloride (20 mL) was added trifluoroacetic acid (4 mL). The resulting solution was stirred for 2 hours, then poured onto saturated aqueous sodium bicarbonate, and extracted with methylene chloride (3×50 mL). The combined organic layers were dried over... | CC(C)(C)[Si](Oc1ccc(F)c(CN2CCNCC2=O)c1)(c1ccccc1)c1ccccc1 | null | null | null |
900,516 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | [OH:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:14]=[CH:15][CH:16]=3)[N:11]=[CH:10][C:9]=2[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:23])[CH:5]=[CH:6][CH:7]=1.C[O:31][C:32](=[O:43])[C:33]1[CH:38]=[CH:37][C:36]([CH2:39]Br)=[C:35]([O:41][CH3:42])[CH:34]=1.[OH-].[Na+]>C... | O=C(c1ccccc1)c1cnc2c(C(F)(F)F)cccc2c1-c1cccc(O)c1 | COC(=O)c1ccc(CBr)c(OC)c1 | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from [4-(3-hydroxyphenyl)-8-(trifluoromethyl)-quinolin-3-yl](phenyl)methanone and 4-Bromomethyl-3-methoxy-benzoic acid methyl ester following the procedure of Example 478 then hydrolysis using sodium hydroxide in THF:MeOH (1:2) at RT for 12 hr, the reaction mixture was acidified and conc... | COc1cc(C(=O)O)ccc1COc1cccc(-c2c(C(=O)c3ccccc3)cnc3c(C(F)(F)F)cccc23)c1 | null | null | null |
865,277 | ord_dataset-b8b98725045d45bdbd73512048f4b47e | null | 2009-01-01T00:02:00 | true | [C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][C:14]([CH2:18][S:19]([C:22]3[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[CH:24][CH:23]=3)(=[O:21])=[O:20])([OH:17])[CH2:13][CH2:12]2)=[CH:5][CH:4]=1)#[N:2].[OH-].[Na+:33]>CO>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][C:14... | COC(=O)c1ccc(S(=O)(=O)CC2(O)CCN(CCc3ccc(C#N)cc3)CC2)cc1 | null | null | [Na+] | [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 | 25 | 72 | To a solution of the compound (70 mg) obtained in Example 46 in methanol (2.0 mL) was added 2 N aqueous sodium hydroxide solution (0.080 mL), followed by stirring at room temperature for three days. The solvent was removed under reduced pressure, the residue was mixed with ethyl acetate (4 mL) and was stirred for one h... | N#Cc1ccc(CCN2CCC(O)(CS(=O)(=O)c3ccc(C(=O)[O-])cc3)CC2)cc1 | null | null | null |
1,391,787 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5](I)=[CH:4][C:3]=1[CH3:10].[CH3:11][C:12]([OH:29])([CH3:28])[CH2:13][N:14]1[CH:18]=[C:17](B2OC(C)(C)C(C)(C)O2)[CH:16]=[N:15]1.C([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:17]2[CH:16]=[N:15][N:14]([CH2:13][C:12]([CH3:28])([OH:29])[CH3:11])[CH:18]=2)=... | Cc1cc(I)cc(C)c1Br | CC(C)(O)Cn1cc(B2OC(C)(C)C(C)(C)O2)cn1 | null | O=C([O-])[O-] | [Na+] | 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 | 60 | 3 | A mixture of 2-bromo-5-iodo-1,3-dimethylbenzene (1.00 g), 2-methyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propan-2-ol (1.11 g), and 2 M aqueous Na2CO3 solution (4.0 mL) in N,N-dimethylformamide is purged with argon for 3 min. [1,1′-Bis(diphenylphosphino)-ferrocene]-dichloropalladium dichloro... | Cc1cc(-c2cnn(CC(C)(C)O)c2)cc(C)c1Br | null | null | null |
884,319 | ord_dataset-d728a2f811c0424cbcdb5a84d02b93ae | null | 2009-01-01T00:06:00 | true | [C:1]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1)(=[O:4])[CH:2]=[CH2:3].[S:15]1[CH:19]=[CH:18][N:17]=[C:16]1[CH:20]=[O:21].C1N2CCN(CC2)C1>>[OH:21][CH:20]([C:16]1[S:15][CH:19]=[CH:18][N:17]=1)[C:2](=[CH2:3])[C:1]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1)=[O:4] | O=Cc1nccs1 | C=CC(=O)OCc1ccc(Cl)c(Cl)c1 | null | C1CN2CCN1CC2 | 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 | A mixture of 59 mg (0.26 mmol) of 3,4-dichlorophenylmethyl acrylate, 27 mg (0.24 mmol) of 2-thiazolecarboxaldehyde, and 31 mg (0.28 mmol) of DABCO was thoroughly shaken on a Vortex mixer, and then stored at 0° C. overnight. The product was purified by prep HPLC to give 34 mg (0.10 mmol; 42% yield) of the desired Baylis... | C=C(C(=O)OCc1ccc(Cl)c(Cl)c1)C(O)c1nccs1 | null | 42 | null |
1,656,391 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[N:7][CH:6]=[C:5]2[OH:12].[N+:13]([O-])([OH:15])=[O:14]>OS(O)(=O)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[N:7][C:6]([N+:13]([O-:15])=[O:14])=[C:5]2[OH:12] | O=[N+]([O-])O | Oc1cnnc2ccc(Br)cc12 | null | O=S(=O)(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 | 60 | null | Under N2, an orange solution of 6-bromocinnolin-4-ol (18.5 g, 82 mmol) in HNO3 (90 mL, 82 mmol) was cooled to 0° C., and H2SO4 (30 mL) was added. The resulting mixture was then heated at 60° C. for 3 h. After the reaction went to completion as monitored by LC-MS, the reaction mixture was cooled to 0° C., and was then q... | O=[N+]([O-])c1nnc2ccc(Br)cc2c1O | null | 58.7 | null |
913,981 | ord_dataset-c663259b80f947e2a8923796fb0e9a6b | null | 2009-01-01T00:10:00 | true | [CH:1]1([N:6]2[CH2:11][CH2:10][N:9]([C:12]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[NH:19][C:18]([C:23]([N:25]3[CH2:30][CH2:29][C:28]([F:32])([F:31])[CH2:27][CH2:26]3)=[O:24])=[CH:17]4)=[O:13])[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH:35]1([CH2:38]Br)[CH2:37][CH2:36]1>CN(C)C=O>[CH:1]1([N:6]2[C... | BrCC1CC1 | O=C(c1ccc2[nH]c(C(=O)N3CCC(F)(F)CC3)cc2c1)N1CCN(C2CCCC2)CC1 | null | [H-] | [Na+] | 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 | null | null | The title compound was synthesized in analogy to example 51, from [5-(4-cyclopentyl-piperazine-1-carbonyl)-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanone (example 8), sodium hydride and cyclopropylmethyl bromide in N,N-dimethylformamide give the desired product as a colorless foam (44%). | O=C(c1ccc2c(c1)cc(C(=O)N1CCC(F)(F)CC1)n2CC1CC1)N1CCN(C2CCCC2)CC1 | null | 44 | null |
1,691,392 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:11]([NH:21]C(=O)C)[N:10]([CH3:25])[N:9]=1>C(O)C.[OH-].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]([C:13]#[C:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[C:11]([NH2:21])[N:... | CC(=O)Nc1c(C#Cc2ccccc2)c(-c2ccccc2Cl)nn1C | null | 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 | A solution of N-(3-(2-chlorophenyl)-1-methyl-4-(phenylethynyl)-1H-pyrazol-5-yl)acetamide (170 mg, 0.49 mmol) in ethanol (1 mL) and 25% NaOH (1.4 mL) was heated to 85° C. for 30 h. The reaction mixture was partitioned between ethyl acetate and water. The aqueous phase was washed with ethyl acetate and the organic phases... | Cn1nc(-c2ccccc2Cl)c(C#Cc2ccccc2)c1N | null | 90.2 | null |
962,716 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][CH:35]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([CH2:15][O:16][CH2:17][CH2:18]Cl)=[CH:12][CH:13]=2)[C:8]([S:20]([C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][CH:24]=2)(=[O:22])=[O:21])=[N:7]1.[CH3:36][NH:37][CH3:38]>CS(C)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([C... | O=S(=O)(c1cccc2ccccc12)c1nn(Cc2cccc(Cl)c2)c2ccc(COCCCl)cc12 | CNC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | O | null | null | null | null | null | null | null | null | null | 100 | 4 | A mixture of 1-(3-chlorobenzyl)-5-(2-chloroethoxymethy)-3-(1-naphthylsulfony)-1H-indazole (0.08 g, 0.16 mmoles) and dimethylamine (0.28 ml, 0.56 mmoles) in DMSO (1 mL) was stirred under nitrogen at 100° C. for 4 hours. Mixture was cooled to room temperature, diluted with water, extracted with EtOAc, washed with water (... | CN(C)CCOCc1ccc2c(c1)c(S(=O)(=O)c1cccc3ccccc13)nn2Cc1cccc(Cl)c1 | null | 93.7 | null |
1,058,484 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [F:1][C:2]1[CH:11]=[CH:10][C:9]([CH2:12][NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([N:13]([CH2:12][C:9]2[CH:10]=[CH:... | CCCCCCNCc1ccc(F)c(C(=O)OC)c1 | O=S(=O)(Cl)c1ccc(Br)cc1 | null | O=C([O-])O | [Na+] | 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 | 2 | To a solution of methyl 2-fluoro-5-[(hexylamino)methyl]benzoate in DCM (13 mL) were added 4-bromobenzenesulfonyl chloride (200 mg; 0.79 mmol) and TEA (0.13 mL; 0.94 mmol). The reaction mixture was stirred at room temperature for 2 hours under N2 atmosphere. The mixture was poured into a saturated solution of NaHCO3 and... | CCCCCCN(Cc1ccc(F)c(C(=O)OC)c1)S(=O)(=O)c1ccc(Br)cc1 | null | 25 | null |
947,718 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | ClC(Cl)(Cl)[C:3]([C:5]1[N:14]2[C:8]([CH2:9][N:10]([C:19]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[CH3:33])=[C:23]([CH3:34])[CH:22]=3)=[O:20])[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13]2)=[CH:7][CH:6]=1)=[O:4].[F:37][C:38]([F:49])([F:48])[O:39][C:40]1[CH:47]=[CH:46][C:43]([CH2... | Cc1ccccc1-c1ccc(C(=O)N2Cc3ccc(C(=O)C(Cl)(Cl)Cl)n3Cc3ccccc32)cc1C | NCc1ccc(OC(F)(F)F)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 title compound was synthesized in the manner of Example 13 from 2,2,2-trichloro-1-{10-[(2,2′-dimethyl-1,1′-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone of Example 6 and 4-trifluoromethoxy benzylamine, m.p. 147-149° C. MS [(+)ESI, m/z]: 608 [M+H]+ Anal. Calcd for C36H30F3N3... | Cc1ccccc1-c1ccc(C(=O)N2Cc3ccc(C(=O)NCc4ccc(OC(F)(F)F)cc4)n3Cc3ccccc32)cc1C | null | null | null |
1,424,575 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | C(OC(=O)[N:7]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([NH:19][C:20]2[CH:25]=[N:24][C:23]([C:26]#[N:27])=[CH:22][N:21]=2)=[O:18])=[CH:12][CH:11]=1)(C)(C)C.Cl>O1CCOCC1>[CH2:28]([NH:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17]([NH:19][C:... | CC(C)(C)OC(=O)N(CCc1ccc(NC(=O)Nc2cnc(C#N)cn2)cc1)Cc1ccccc1 | 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 | 25 | 8 | Benzyl-(2-{4-[3-(5-cyano-pyrazin-2-yl)-ureido]-phenyl}-ethyl)-carbamic acid tert-butyl ester (1 mmol) was treated with 4N HCl in dioxane (10 ml) and stirred overnight at room temperature. The product was precipitated by addition of dry ether. The crude was purified by column using 0-100% 7 N NH3/MeOH in DCM to afford t... | N#Cc1cnc(NC(=O)Nc2ccc(CCNCc3ccccc3)cc2)cn1 | null | null | null |
353,021 | ord_dataset-127eb5fdd5b4402e92b51d0b55a5dcb5 | null | 1997-01-01T00:01:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][C:3]=1[OH:12].C(OCC)(=O)C.C(=O)([O-])O.[Na+].Br[CH:25]([CH2:29][CH2:30][CH2:31][CH3:32])[C:26](Br)=[O:27]>O>[CH2:29]([CH:25]1[C:26](=[O:27])[NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][C:3]=2[O:12]1)[CH2:30][CH2:31][CH3:32] | CCCCC(Br)C(=O)Br | COC(=O)c1ccc(N)c(O)c1 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | 0.17 | To a solution of 2-amino-5-methoxycarbonylphenol [Tetrahedron, 4.6 (15), 5177-5186 (1990)] (8.0 g) in a mixed solvent of ethyl acetate (200 ml) and water (200 ml) were added sodium hydrogen carbonate (11.18 g) and 2-bromohexanoyl bromide (12.73 g) and the mixture was stirred at room temperature for 10 minutes. The orga... | CCCCC1Oc2cc(C(=O)OC)ccc2NC1=O | null | 81.7 | null |
1,124,350 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | C([O:4][CH2:5][C@H:6]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH3:33])[C:14]=2[NH:18][C:19](=[O:32])[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[C:23]([F:31])[CH:22]=2)[C:9]1=[O:34])[CH3:7])(=O)C.C(=O)([O-])[O-].[K+].[K+].CO>O>[F:31][C:23]1[CH:22]=[C:21]([CH2:20][C:19]([NH:18][... | CC(=O)OC[C@@H](C)n1ccc2c(NC(=O)Cc3ccc(C(F)(F)F)c(F)c3)c(C)ccc2c1=O | null | null | O=C([O-])[O-] | [K+] | 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 | 25 | 0.33 | A round bottom flask was charged with (R)-2-(5-(2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl acetate (300.00 mg, 0.62704 mmol), potassium carbonate (260 mg, 0.0019 mol), methanol (20 mL, 0.4 mol) and 2 drops of water. The reaction was stirred at room temperature for 20 minu... | Cc1ccc2c(=O)n([C@H](C)CO)ccc2c1NC(=O)Cc1ccc(C(F)(F)F)c(F)c1 | null | null | null |
966,908 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | C(OC([N:11]1[C:19]2[C:14](=[C:15]3[O:23][C:22]([CH:24]([CH3:26])[CH3:25])=[C:21]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=4)[C:20](=[O:34])[C:16]3=[CH:17][CH:18]=2)[C:13]([CH3:35])=[CH:12]1)=O)C1C=CC=CC=1>O1CCCC1.C(O)C.Cl.[Pd]>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([C:21]2[C:20](=[O:34])[C:16]3[C:15]([O:23][C:... | Cc1cn(C(=O)OCc2ccccc2)c2ccc3c(=O)c(-c4ccc(Cl)cc4)c(C(C)C)oc3c12 | null | null | [Pd] | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 3.5 | A stirred suspension of 3-(4-chlorophenyl)-2-isopropyl-9-methyl-4-oxo-4H-pyrano[2,3-e]indole-7-carboxylic acid benzyl ester and its positional isomer (0.063 g, 0.13 mmol) and 20% Pd on activated carbon (0.013 g) in tetrahydrofuran (1.5 ml), ethanol (1.5 ml) and 5M HCl solution (0.75 ml) is stirred under a hydrogen atmo... | Cc1c[nH]c2ccc3c(=O)c(-c4ccc(Cl)cc4)c(C(C)C)oc3c12 | null | null | null |
1,085,430 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([CH:17]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[C:18]([OH:20])=O)=[C:15]3[C:10]([CH:11]=[CH:12][CH:13]=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH2:31]([O:33][C:34](=[O:42])[C:35]1[CH:40]=[CH:39][C:38]([NH2:41])=[CH:37][CH:36]=1)[CH3:32]>CN(C1C=CN=CC=1)C>[CH2:... | CCOC(=O)c1ccc(N)cc1 | O=C(O)C(c1c2ccccc2nn1-c1ccc(Cl)cc1)C1CCCCC1 | null | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | In analogy to the procedure described in example 6, [2-(4-chloro-phenyl)-2H-indazol-3-yl]-cyclohexyl-acetic acid was converted into the corresponding acid chloride with thionyl chloride which subsequently reacted with 4-amino-benzoic acid ethyl ester (CAS Reg. No. 94-09-7]) in the presence of DMAP to give the title com... | CCOC(=O)c1ccc(NC(=O)C(c2c3ccccc3nn2-c2ccc(Cl)cc2)C2CCCCC2)cc1 | null | null | null |
706,205 | ord_dataset-c408dfed796e4354b61e312e67f7143f | null | 2006-01-01T00:04:00 | true | [C:1]([O:5][C:6](=[O:32])[NH:7][CH2:8][C:9]1[N:10]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:11](=[O:27])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:16][C:15]([CH2:25][NH2:26])=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2].[C:33](Cl)(=[O:37])[CH:34]([CH3:36])[CH3:35].C(N(CC)CC)C>O1CCCC1>[C:1]([O:5... | CC(C)Cn1c(CNC(=O)OC(C)(C)C)c(-c2ccccc2)c2cc(CN)ccc2c1=O | CC(C)C(=O)Cl | null | null | null | null | 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 | 25 | 4 | To a solution of crude tert-butyl[6-(aminomethyl)-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.016 g) (Example 285) in tetrahydrofuran (2 mL) was added isobutyryl chloride (0.038 mL, 0.36 mmol) and triethylamine (0.050 mL, 0.36 mmol), and the mixture was stirred at room temperature for 4 h. ... | CC(C)Cn1c(CNC(=O)OC(C)(C)C)c(-c2ccccc2)c2cc(CNC(=O)C(C)C)ccc2c1=O | null | 592.2 | null |
1,699,134 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | COC([C:5]1([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:9][CH2:8][C:7]([CH2:11][Cl:12])([CH3:10])[C:6]1=[O:13])=O.O.C1(C)C(S(O)(=O)=O)=CC=CC=1>O>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH:5]2[C:6](=[O:13])[C:7]([CH2:11][Cl:12])([CH3:10])[CH2:8][CH2:9]2)=[CH:20][CH:19]=1 | COC(=O)C1(Cc2ccc(Cl)cc2)CCC(C)(CCl)C1=O | null | null | Cc1ccccc1S(=O)(=O)O | null | 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 | 120 | 1.5 | To 1.00 g of Compound 3-1-3 synthesized in Production Example 4, 0.578 g of toluenesulfonic acid monohydrate and 100 mg of water were added, and the resulting mixture was stirred in an oil bath of 120° C. for 1.5 hours. After the reaction, water was added to the reaction solution thus obtained, and extraction with ethy... | CC1(CCl)CCC(Cc2ccc(Cl)cc2)C1=O | null | 91.3 | null |
575,472 | ord_dataset-f4512fe8cd804ac79da66cbc0c2b9d42 | null | 2002-01-01T00:12:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].Br[C:17]1[CH:27]=[CH:26][CH:25]=[CH:24][C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:17][C:18]=2[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=... | COc1cc(B(O)O)cc(OC)c1OC | CCOC(=O)c1ccccc1Br | 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 | 3,4,5-Trimethoxyphenylboronic acid (639 mg) and ethyl 2-bromobenzoate (479 mg) were condensed in the same manner as described in Preparation Example 1 to give the title compound. | CCOC(=O)c1ccccc1-c1cc(OC)c(OC)c(OC)c1 | null | null | null |
1,483,401 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [OH:1][CH:2]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:21]=[C:20]([C:22]3[O:26][N:25]=[C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:23]=3[C:33]([F:36])([F:35])[F:34])[O:19][N:18]=2)=[CH:13][CH:12]=1)[C:3]([NH:5][CH2:6][CH2:7][C:8]([OH:10])=O)=[O:4].C[N:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.CN(C(ON1N=NC2C=... | CN1CCOCC1 | O=C(O)CCNC(=O)C(O)c1ccc(-c2noc(-c3onc(-c4ccccc4)c3C(F)(F)F)n2)cc1 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | 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 | null | 1 | (R/S)-3-(2-Hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetamido)propanoic acid (Int-V, 25 mg, 0.050 mmol), 3-methoxyazetidine, HCl (6.15 mg, 0.050 mmol), 4-methylmorpholine (20.13 mg, 0.199 mmol), and HATU (24.60 mg, 0.065 mmol) were added to DMF (3 mL). This was stirred for... | COC1CN(C(=O)CCNC(=O)C(O)c2ccc(-c3noc(-c4onc(-c5ccccc5)c4C(F)(F)F)n3)cc2)C1 | null | 50 | null |
697,968 | ord_dataset-4e9c2fa02a7544fd839206719263345f | null | 2006-01-01T00:02:00 | true | FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[CH:12][CH:13]=2)[CH:8]=1)(=O)=O.[CH3:21][N:22](C=O)C>[C-]#N.[Zn+2].[C-]#N.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=... | CN(C)C=O | COc1ccc2ccc(OS(=O)(=O)C(F)(F)F)cc2c1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | [C-]#N | [Zn+2] | 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 | 80 | null | A solution of 7-methoxy-2-naphthyl trifluoromethanesulfonate (4.95 g, 16.1 mmol) in DMF (20 mL) is degassed by repeatedly evacuating the flask then flushing with N2. Zinc cyanide (1.13 g, 9.7 mmol) is added followed by Pd(PPh3)4 (930 mg, 0.81 mmol). The resulting mixture is again degassed and heated to 80° C. for 3 hou... | COc1ccc2ccc(C#N)cc2c1 | null | 80 | null |
24,149 | ord_dataset-fcf7c02bbb814fe696760b5fbfee16bb | null | 1977-01-01T00:05:00 | true | [N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[N:11]=2)=[CH:6][CH:5]=1)([O-])=O.[BH4-].[Na+].[S]>O1CCCC1>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[N:11]=2)=[CH:6][CH:5]=1 | O=[N+]([O-])c1ccc(-c2nc(-c3ccccn3)no2)cc1 | null | null | [BH4-] | [Na+] | [S] | 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 | null | A solution of 2.5 g (0.01 mole) of 5-(4-nitrophenyl)-3-(2-pyridyl)-1,2,4-oxadiazole in 200 ml of tetrahydrofuran is added slowly to a solution of NaBH2S3 which is prepared by stirring 0.36 g of NaBH4 and 0.96 g of sulfur in 50 ml of tetrahydrofuran for 0.5 hour. The reaction mixture is then refluxed for 24 hours. The m... | Nc1ccc(-c2nc(-c3ccccn3)no2)cc1 | null | 42 | null |
1,441,681 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1Br.[Mg].II.[CH:14](=[O:20])[C:15]1[O:19][CH:18]=[CH:17][CH:16]=1>O1CCCC1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[CH:14]([C:15]1[O:19][CH:18]=[CH:17][CH:16]=1)[OH:20] | Cc1cc(C)c(Br)c(C)c1 | O=Cc1ccco1 | null | II | [Mg] | 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 | 0.42 | A solution of 2,4,6-trimethyl-1-bromobenzene (30.9 g, 155 mmol) in tetrahydrofuran (100 ml) is added slowly to magnesium turnings (3.77 g, 155 mmol), until the magnesium is just covered. A small quantity of iodine is added and the mixture is allowed to stand at room temperature for 25 minutes and then heated and stirre... | Cc1cc(C)c(C(O)c2ccco2)c(C)c1 | null | null | null |
643,117 | ord_dataset-ce71a906ea9c4399a2014cbaaff88c8f | null | 2004-01-01T00:07:00 | true | [C:1]1([C@H:7]2[CH2:12][CH2:11][C@H:10]([NH:13][CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:23](Cl)Cl.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>CO.O>[CH3:23][N:13]([C@H:10]1[CH2:9][CH2:8][C@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:... | ClCCl | Oc1ccc(CCN[C@H]2CC[C@H](c3ccccc3)CC2)cc1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | [Na+] | [OH-] | 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 | null | 12 | To a stirred solution of trans-4-[2-(4-phenylcyclohexylamino)ethyl]phenol (380 mg, 1.3 mmol) in MeOH (5 mL), H2O (0.5 mL), and CH2Cl2 (5 mL) was added ρformaldehyde (200 mg, 6.5 mmol). After stirring for 15 minutes NaBH(OAc)3 (340 mg, 1.6 mmol) was added, and the reaction mixture was stirred for 12 hours. Additional Na... | CN(CCc1ccc(O)cc1)[C@H]1CC[C@H](c2ccccc2)CC1 | null | null | null |
301,538 | ord_dataset-9ad0840101374618a7d5c4e4521c82d1 | null | 1994-01-01T00:12:00 | true | C([NH:4][C:5]1[CH:9]=[CH:8][S:7][C:6]=1[S:10][C:11](=O)[CH3:12])(=O)C>C1(C)C=CC=CC=1>[CH3:12][C:11]1[S:10][C:6]2[S:7][CH:8]=[CH:9][C:5]=2[N:4]=1 | CC(=O)Nc1ccsc1SC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 205 | null | A solution of 660 mg (3.1 mmol) of N-acetyl-2-(acetylthio)-3-thiophenamine in 8 mL of toluene was degassed in a Pyrex robe under high vaccuum. The robe was subsequently sealed under high vaccuum and heated at 205° C. for 5 hr. Chromatographic separation on silica gel using hexane/EtOAc (5:1 ) gave 440 mg (80%) of the t... | Cc1nc2ccsc2s1 | null | 91.4 | null |
1,499,080 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [CH:1]([C@@H:4]1[N:8]([C:9]2[CH:14]=[CH:13][N:12]3[N:15]=[CH:16][C:17]([C:18]4[CH:23]=[CH:22][C:21]([C:24]5[N:28]=[CH:27][N:26](COCC[Si](C)(C)C)[N:25]=5)=[CH:20][CH:19]=4)=[C:11]3[N:10]=2)[C:7](=[O:37])[NH:6][CH2:5]1)([CH3:3])[CH3:2].C([O-])(O)=O.[Na+]>CCO>[NH:26]1[CH:27]=[N:28][C:24]([C:21]2[CH:20]=[CH:19][C:18]([C:17... | CC(C)[C@H]1CNC(=O)N1c1ccn2ncc(-c3ccc(-c4ncn(COCC[Si](C)(C)C)n4)cc3)c2n1 | null | null | O=C([O-])O | [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 | null | null | A mixture of (S)-5-isopropyl-1-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-2-one (Example 25, Step 4, 12 mg, 0.023 mmol) and EtOH/6N aqueous HCl (1:2, 0.5 mL total) was heated at reflux for 3 hours. After cooling, the reaction mixture was neutraliz... | CC(C)[C@H]1CNC(=O)N1c1ccn2ncc(-c3ccc(-c4nc[nH]n4)cc3)c2n1 | null | 67.2 | null |
1,769,592 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | Cl.[CH:2]1([NH:8][C:9]2[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=[C:11]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[N:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:25]C1C(CN)=NC=CC=1>>[CH:2]1([NH:8][C:9]2[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=[C:11]([NH:17][CH2:18][C:19]3[C:24]([CH3:25])=[CH:23][CH:2... | Cc1cccnc1CN | Cc1nc(NCc2ccccn2)nc(NC2CCCCC2)c1C | 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 | The titled compound was synthesized according to the general procedure described for preparation of N4-cyclohexyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine (Example 1) using [(3-methylpyridin-2-yl)methyl]amine instead of (pyridin-2-ylmethyl)amine. The crude product was purified by crystallization from ... | Cc1cccnc1CNc1nc(C)c(C)c(NC2CCCCC2)n1 | null | null | null |
780,954 | ord_dataset-8034115bd2ec4d3e95bd3ff7cfde0bde | null | 2007-01-01T00:07:00 | true | [C:1]1(C2C=CC=CC=2)[CH:6]=[CH:5][C:4]([CH2:7][C:8]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:15]([O:27][CH2:28]C3C=CC=CC=3)[CH:14]=2)=O)=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:43])=O.[BH4-].[Na+]>C(#N)C.Cl>[ClH:43].[CH2:28]([O:27][C:15]1[CH:14]=[C:13]2[C:... | O=P(Cl)(Cl)Cl | O=C(Cc1ccc(-c2ccccc2)cc1)NCCc1ccc(OCc2ccccc2)c(OCc2ccccc2)c1 | null | Cl | [BH4-] | [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 | null | 8 | 6,7-bis-benzyloxy-1-biphenyl-4-ylmethyl-1,2,3,4-tetrahydro-isoquinoline hydrochloride (2) was prepared as follows: A stirred solution of 3 g (5.69 mmol) of 2-biphenyl-4-yl-N-[2-(3,4-bis-benzyloxy-phenyl)-ethyl]-acetamide and 5.6 ml (60 mmol) of phosphorus oxychloride in 25 ml of anhydrous acetonitrile was refluxed for ... | c1ccc(COc2cc3c(cc2OCc2ccccc2)C(Cc2ccc(-c4ccccc4)cc2)NCC3)cc1 | null | null | null |
1,358,918 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@@:13]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)([CH2:16][CH2:17][CH2:18][OH:19])[O:12][C:11]2=[O:27])[CH3:9])=[CH:4][CH:3]=1.Br[C:29]1[CH:34]=[C:33]([CH3:35])[N+:32]([O-:36])=[C:31]([CH3:37])[CH:30]=1>>[F:26][C:23]1[CH:24]=[CH:25][C:20]([C@:13]2... | C[C@@H](c1ccc(Br)cc1)N1CC[C@](CCCO)(c2ccc(F)cc2)OC1=O | Cc1cc(Br)cc(C)[n+]1[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 | The title compound was prepared from (R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-6-(3-hydroxypropyl)-1,3-oxazinan-2-one following procedures analogous to those described in Example 313 Steps 3 and 4 using 4-bromo-2,6-dimethylpyridine-N-oxide in Step 4. LC-MS Method 2 tR=1.092, m/z=479.1; 1H NMR (CDCl3) 1.38 (... | Cc1cc(-c2ccc([C@H](C)N3CC[C@](CCCO)(c4ccc(F)cc4)OC3=O)cc2)cc(C)[n+]1[O-] | null | null | null |
1,543,998 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5](F)=[CH:4][C:3]=1[O:9][CH3:10].[CH2:11]([S-:13])[CH3:12].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:13][CH2:11][CH3:12])=[CH:4][C:3]=1[O:9][CH3:10] | CC[S-] | COc1cc(F)ccc1Br | null | [Na+] | 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 | null | 72 | To a room temperature solution of 1-bromo-4-fluoro-2-methoxybenzene (5.00 g, 24.39 mmol) in DMF (15 mL) was added sodium ethanethiolate (2.66 g, 31.71 mmol) and the resulting reaction mixture was stirred for 72 hours. The reaction mixture was partitioned between water (20 mL) and EtOAc (50 mL). The organic layer was se... | CCSc1ccc(Br)c(OC)c1 | null | 17 | null |
769,178 | ord_dataset-8214eb8444a44dc2900ccb42dbeff15e | null | 2007-01-01T00:05:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([N+:24]([O-:26])=[O:25])[C:5]([O:22]C)=[C:6]([CH:21]=1)[CH:7]=[C:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1.[Cl-].[Li+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([N+:24]([O-:26])=[O:25])[C:5]([OH:22])=[C:6]([CH:21]=1)[CH:7]=[C:8]1[CH2:9][CH2:10][N... | COc1c(C=C2CCN(C(=O)OC(C)(C)C)CC2)cc(Br)cc1[N+](=O)[O-] | null | null | [Cl-] | [Li+] | 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 | 120 | 4 | A mixture of tert-butyl 4-(5-bromo-2-methoxy-3-nitrobenzylidene)piperidine-1-carboxylate (2.5 g, 5.9 mmol) and lithium chloride (1 g) in anhydrous N,N-dimethylformamide was stirred at 120° C. for 4 h. It was allowed to cool to room temperature and evaporated in vacuo. The residue was treated with water (50 mL) and extr... | CC(C)(C)OC(=O)N1CCC(=Cc2cc(Br)cc([N+](=O)[O-])c2O)CC1 | null | null | null |
40,909 | ord_dataset-2345345e84034af393f969fc5e7741b6 | null | 1978-01-01T00:05:00 | true | [CH2:1]([NH:8][CH2:9][CH2:10][C:11]([OH:24])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:25][CH2:26][C:27](Cl)=[O:28]>C(N(C(C)C)CC)(C)C.C(Cl)Cl>[CH2:1]([N:8]([CH2:9][CH2:10][C:11]([OH:24])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20... | OC(CCNCc1ccccc1)(c1ccccc1)c1ccccc1 | O=C(Cl)CCl | 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 | ClCCl | null | null | null | null | null | null | null | null | null | null | null | To the stirred solution of 15.6 g of N-benzyl-3-hydroxy-3,3-diphenylpropylamine in 7.0 g of di-isopropylethylamine and 150 ml of methylene chloride, that of 5.88 g of chloroacetyl chloride in 50 ml of methylene chloride is added dropwise while stirring and cooling with an ice-bath. Thereupon the solution is stirred for... | O=C(CCl)N(CCC(O)(c1ccccc1)c1ccccc1)Cc1ccccc1 | null | null | null |
732,758 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:14](=[O:15])[C:13]([O:16][CH2:17][C:18]([OH:21])([CH3:20])[CH3:19])=[C:12]([C:22]3[CH:27]=[CH:26][C:25]([S:28]([NH2:31])(=[O:30])=[O:29])=[CH:24][CH:23]=3)[CH:11]=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[C:32](OC(=O)C)(=[O:34])[CH3:33].C(N(CC)CC)C>CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([N... | CC(C)(O)COc1c(-c2ccc(S(N)(=O)=O)cc2)cnn(-c2ccc(F)c(Cl)c2)c1=O | CC(=O)OC(C)=O | null | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 25 | 16 | A mixture of 2-(3-chloro-4-fluorophenyl)-4-(2-hydroxy-2-methyl-1-propoxy)-5-[4-(aminosulfonyl)phenyl]-3(2H)-pyridazinone (Example 480, 1 equivalent), acetic anhydride (3 equivalents), 4-(dimethylamino)pyridine (0.3 equivalents), and triethylamine (1.2 equivalents) is stirred at room temperature for 16 hours. The reacti... | CC(=O)NS(=O)(=O)c1ccc(-c2cnn(-c3ccc(F)c(Cl)c3)c(=O)c2OCC(C)(C)O)cc1 | null | null | null |
1,172,519 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | [F:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[N:17]=[C:18]([CH2:21][O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[NH:19][CH:20]=3)=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:3]=1[NH2:4].[N-:29]([C:32]#[N:33])[C:30]#[N:31].[Na+]>CN(C)C=O.Cl>[C:30]([N:29]=[C:32]([NH2:33])[NH:4][C:3]1[CH:5]=[CH:6][C:7]([O... | N#C[N-]C#N | Nc1ccc(Oc2ccc(-c3c[nH]c(COc4ccccc4)n3)cc2)cc1F | null | Cl | [Na+] | 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 | null | null | In a sealed glass tube suitable for microwave heating, the compound 2-fluoro-4-{4-[2-(phenoxymethyl)-1H-imidazol-4-yl]phenoxy}aniline (0.1 g, 0.27 mmol) and sodium dicyanamide (37 mg, 0.4 mmol) in 2.5 ml of dimethylformamide and 0.5 ml of hydrochloric acid 1N are heated at 75° C. in a microwave oven (Biotage, Emrys Opt... | N#CN=C(N)Nc1ccc(Oc2ccc(-c3c[nH]c(COc4ccccc4)n3)cc2)cc1F | null | 31 | null |
711,491 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | [CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][C@H:13]([OH:21])[CH2:14][N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[CH:7][C:5]=2[N:6]=1.[C:22]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[N:36]=[C:35]([CH2:37]Cl)[O:34][N:33]=2)=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23]>CN(C)C.C(O)C>[C:22]([C:26]1[CH:27]=[C... | CC(C)(C)c1ccc(-c2noc(CCl)n2)cc1 | Cc1nc2cc(OC[C@H](O)CN3CCNCC3)ccc2s1 | null | CN(C)C | 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 | 8 | A solution of (2R)-1-(2-methylbenzothiazol-5-yloxy)-3-piperazinylpropan-2-ol, a compound of formula (6) (75 mg, 0.14 mmol), and 3-(4-tert-butylphenyl)-5-chloromethyl-1,2,4-oxadiazole (40 mg, 0.16 mmol) in 10% trimethylamine/ethanol, was heated to 73° C. and allowed to stir overnight. The solvent was evaporated under re... | Cc1nc2cc(OC[C@H](O)CN3CCN(Cc4nc(-c5ccc(C(C)(C)C)cc5)no4)CC3)ccc2s1 | null | null | null |
1,324,242 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [NH2:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[I:14]I>C1COCC1>[F:8][C:7]1[C:2]([NH2:1])=[N:3][CH:4]=[CH:5][C:6]=1[I:14] | Nc1ncccc1F | II | null | [Li]CCCC | 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 | -78 | 1 | A solution of 2-amino-3-fluoropyridine (1.0 g, 8.9 mmol) in anhydrous THF (40 ml) was treated dropwise at −78° C. with n-butyllithium (1.6 M in hexanes, 13.9 ml, 22.3 mmol). Following the addition, the mixture was stirred at −78° C. for 1 h, then a solution of iodine (10.2 g, 40.1 mmol) in THF (20 ml) was added. The mi... | Nc1nccc(I)c1F | null | null | null |
1,407,094 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [CH:1]1([C:4]2[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=2[CH2:6][N:7]2[C:12]3[N:13]=[C:14]([S:17][CH3:18])[N:15]=[CH:16][C:11]=3[CH:10]=[CH:9][C:8]2=[O:19])[CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:32])C=1>ClCCl>[CH:1]1([C:4]2[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=2[CH2:6][N:7]2[C:12]3[N:13]=[C:14]([S:17]([CH3:18])=[O:32])[N:15]=[CH:... | O=C(OO)c1cccc(Cl)c1 | CSc1ncc2ccc(=O)n(Cc3ccccc3C3CC3)c2n1 | 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 | 18 | To a solution of 8-(2-cyclopropylbenzyl)-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (88 mg, 0.27 mmol) in dichloromethane (1 mL) was added 3-chloroperbenzoic acid (70%, 67 mg, 0.27 mmol) at 0-5° C. and the mixture was stirred at room temperature for 18 h. After completion, it was diluted with dichloromethane (10 mL... | CS(=O)c1ncc2ccc(=O)n(Cc3ccccc3C3CC3)c2n1 | null | 85.2 | null |
1,130,307 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | [CH3:1][N:2]([CH3:18])[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][C:7]2[CH:11]=[C:12]([N+:15]([O-])=O)[CH:13]=[CH:14][C:6]1=2>[Pd]>[CH3:1][N:2]([CH3:18])[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][C:7]2[CH:11]=[C:12]([NH2:15])[CH:13]=[CH:14][C:6]1=2 | CN(C)CCN1CCOc2cc([N+](=O)[O-])ccc21 | null | null | [Pd] | 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 | 25 | 3 | A suspension of N,N-dimethyl-2-(7-nitro-2H-benzo[b][1,4]oxazin-4(3H)-yl)ethanamine (210 mg, 0.836 mmol) and Pd—C (10% wt, 89 mg, 0.084 mmol) in dry EtOH (15 mL) was purged with hydrogen gas. The reaction was stirred at room temperature for 3 hours under hydrogen atmosphere (balloon pressure). The reaction mixture was t... | CN(C)CCN1CCOc2cc(N)ccc21 | null | null | null |
126,168 | ord_dataset-fd44e5eeeeb4473cb5fbff2d885d7833 | null | 1985-01-01T00:01:00 | true | [CH3:1][C:2]1[S:6][C:5]([CH:7]=O)=[CH:4][CH:3]=1.C[O:10][CH:11](OC)[CH2:12][NH2:13].O.[BH4-].[Na+]>C1C=CC=CC=1>[OH:10][CH:11]1[CH2:12][NH:13][CH2:7][C:5]2[S:6][C:2]([CH3:1])=[CH:3][C:4]1=2 | Cc1ccc(C=O)s1 | COC(CN)OC | null | [BH4-] | [Na+] | 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 | 60 | 8 | A mixture of 5-methyl-thiophene-2-carboxaldehyde (30 g; 0.237 mole) and aminoacetaldehyde dimethylacetal (27.4 g; 0.261 mole) in benzene (250 ml) is refluxed for 2 hours in a flask provided with a Dean-Stark water separator with overhead condenser. After evaporating to dryness, the residue is dissolved in ethanol (250 ... | Cc1cc2c(s1)CNCC2O | null | 90 | null |
1,064,567 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | Br[C:2]1[C:3]([CH3:21])([CH3:20])[O:4][C:5]2[CH:12]=[C:11]([O:13][CH2:14][O:15][CH3:16])[C:10]([N+:17]([O-:19])=[O:18])=[CH:9][C:6]=2[C:7]=1[OH:8].[OH-].[Na+].O>O1CCOCC1>[O:8]1[CH:7]2[CH:2]1[C:3]([CH3:21])([CH3:20])[O:4][C:5]1[CH:12]=[C:11]([O:13][CH2:14][O:15][CH3:16])[C:10]([N+:17]([O-:19])=[O:18])=[CH:9][C:6]=12 | COCOc1cc2c(cc1[N+](=O)[O-])C(O)=C(Br)C(C)(C)O2 | null | null | [Na+] | [OH-] | null | 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 | null | 2 | To a solution of 3-bromo-7-methoxymethoxy-2,2-dimethyl-6-nitro-1-benzopyran-4-ol (550 mg, 1.52 mmol) in dioxane (5.5 mL), 1 mol/L sodium hydroxide aqueous solution (1.82 mL, 1.82 mmol) was added at room temperature, and the resulting mixture was stirred for 2 hours. Upon the completion of the reaction, water was added ... | COCOc1cc2c(cc1[N+](=O)[O-])C1OC1C(C)(C)O2 | null | 78 | null |
1,607,213 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [F:1][C:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:4][C:3]=1[C:17]1[N:18]=[CH:19][C:20]([NH2:23])=[N:21][CH:22]=1.Br[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31]([N:34]1[CH2:39][CH2:38][NH:37][C:36](=[O:40])[CH2:35]1)(=[O:33])=[O:32]>>[NH2:23][C:20]1[N:21]=[CH:22][C:17]([C:3]2[CH:4]=[CH:5][C:6]([C:25]3[CH:30]... | CC1(C)OB(c2ccc(-c3cnc(N)cn3)c(F)c2)OC1(C)C | O=C1CN(S(=O)(=O)c2ccccc2Br)CCN1 | 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 448 using 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-pyrazin-2-amine and 4-((2-bromophenyl)sulfonyl)piperazin-2-one. MS (ESI): mass calcd. for C20H18FN5O3S, 427.11; m/z found, 428.2 [M+H]+. 1H NMR (400 MHz, CD3OD) δ... | Nc1cnc(-c2ccc(-c3ccccc3S(=O)(=O)N3CCNC(=O)C3)cc2F)cn1 | null | null | null |
1,665,286 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH:5]=O.[CH3:11][S:12]([NH2:15])(=[O:14])=[O:13].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH2:5][NH:15][S:12]([CH3:11])(=[O:14])=[O:13] | O=Cc1cc(F)cc(Br)c1 | CS(N)(=O)=O | 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 | ClCCCl | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of 3-bromo-5-fluorobenzaldehyde (LXXIX) (2.03 g, 10.01 mmol) in DCE (50 mL) was added methanesulfonamide (1.43 g, 15.01 mmol) and TEA (2.79 mL, 20.02 mmol). NaBH(OAc)3 (3.00 g, 14.13 mmol) was added and stirred at room temperature overnight. The solvent was removed under vacuum and the residue was partiti... | CS(=O)(=O)NCc1cc(F)cc(Br)c1 | null | 93.9 | null |
364,643 | ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | null | 1997-01-01T00:05:00 | true | C(O)=O.[C:4]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C@H:13]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[C@H:12]1[CH2:24][O:25]CC1C=CC=CC=1)=[O:10])([CH3:7])([CH3:6])[CH3:5]>CO.[Pd]>[C:4]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C@H:13]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:18])[CH3:19])[... | CC(C)(C)OC(=O)N1CC[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1COCc1ccccc1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=CO | CO | null | null | null | null | null | null | null | null | null | null | null | 0.4 ml of formic acid were added to a solution of 800 mg (1.90 mmol) of (2R,3S)-1-t-butoxycarbonyl-2-benzyloxymethyl-3-t-butyldimethylsilyloxypyrrolidine [which had been prepared from 1-t-butoxycarbonyl-D-seline benzyl ether in a similar manner to that described by W. R. Ewing et al. in Heterocycles, 27, 2843 (1988)] i... | CC(C)(C)OC(=O)N1CC[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO | null | 98.4 | null |
480,073 | ord_dataset-21c1b1c06c7e4e09a38b5b1c71a32e52 | null | 2000-01-01T00:10:00 | true | C(#N)C.[F:4][C:5]1[N:10]=[C:9]([F:11])[C:8]([F:12])=[C:7](F)[C:6]=1[F:14].[C:15]([NH2:19])([CH3:18])([CH3:17])[CH3:16]>C(Cl)(Cl)Cl>[C:15]([NH:19][C:7]1[C:8]([F:12])=[C:9]([F:11])[N:10]=[C:5]([F:4])[C:6]=1[F:14])([CH3:18])([CH3:17])[CH3:16] | Fc1nc(F)c(F)c(F)c1F | CC(C)(C)N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | 25 | null | To 100 ml of acetonitrile was added 24.5 g of pentafluoropyridine, and the mixture was stirred in an ice bath simultaneously with the dropwise addition of 30 g of t-butylamine. When the mixture warmed to room temperature, 150 ml of chloroform was added, and the mixture was washed twice with 800 ml of distilled water. T... | CC(C)(C)Nc1c(F)c(F)nc(F)c1F | null | 71.4 | null |
1,576,440 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.Br[C:44]1[CH:53]=[C:52]2[C:47]([C:48]([C:56]3[CH:61]=[CH:60][C:59]([C:62]([F:65])([F:64])[F:63])=[CH:58][C:57]=3[O:66][CH3:67])=[N:49][C:50]([O:54][CH3:55])=[N:51]2)=[CH:46][CH:45]=1.CCN(C(C)C)C(C)C.[CH2:77]([SH:84])[C:78]1[CH:83]=[C... | COc1nc(-c2ccc(C(F)(F)F)cc2OC)c2ccc(Br)cc2n1 | SCc1ccccc1 | null | [Pd] | CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21 | O=C(/C=C/c1ccccc1)/C=C/c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | 1 | A solution of Pd2(dba)3 (9.20 mg, 10.04 μmol), Xantphos (0.012 g, 0.020 mmol), 7-bromo-2-methoxy-4-(2-methoxy-4-(trifluoromethyl)phenyl)quinazoline (0.166 g, 0.402 mmol), and n,n-diisopropylethylamine (0.211 ml, 1.205 mmol) in 2 mL dioxane was heated to 60° C. and was treated with benzyl mercaptan (0.048 ml, 0.402 mmol... | COc1nc(-c2ccc(C(F)(F)F)cc2OC)c2ccc(SCc3ccccc3)cc2n1 | null | null | null |
820,433 | ord_dataset-ec58fad8331a42c5a67ad75aac6713b4 | null | 2008-01-01T00:05:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][C:27]=1[O:28][CH2:29][C:30]1[N:31]=[C:32]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[O:33][C:34]=1[CH3:35])[CH2:6][O:7][C:8]1[C:12]([CH:13]=O)=[CH:11][N:10]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[N:9]=1.C(OP([CH2:50][C:51]([O:53][... | CCOC(=O)CP(=O)(OCC)OCC | COc1cc(COc2nn(-c3ccc(C(F)(F)F)cc3)cc2C=O)ccc1OCc1nc(-c2ccccc2)oc1C | 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 | null | 0.5 | To a mixture of 3-({3-methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzyl}oxy)-1-[4-(trifluoromethyl)phenyl]-1H-pyrazole-4-carbaldehyde (3.30 g), ethyl diethylphosphonoacetate (1.32 g) and N,N-dimethylformamide (50 mL) was added sodium hydride (60% in oil, 0.236 g) at room temperature, and the mixture was stir... | CCOC(=O)/C=C/c1cn(-c2ccc(C(F)(F)F)cc2)nc1OCc1ccc(OCc2nc(-c3ccccc3)oc2C)c(OC)c1 | null | 69.8 | null |
522,660 | ord_dataset-262b40ea420c471da9b9244fe9b8f645 | null | 2001-01-01T00:10:00 | true | [CH2:1]([C:8]1[O:9][C:10]2[CH:31]=[CH:30][CH:29]=[CH:28][C:11]=2[C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[C:23]([CH3:25])[C:22]([OH:26])=[C:21]([CH3:27])[CH:20]=2)=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[S:33]([C:36]1[CH:44]=[CH:43][C:39]([C:40]([OH:42])=[O:41])=[C:38]([OH:45])[CH:37]=1)... | O=C(O)c1ccc(S(=O)(=O)Cl)cc1O | Cc1cc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc(C)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 | The title compound was prepared from 4′-(2-benzyl-benzofuran-3-yl)-3,5-dimethyl-biphenyl-4-ol and 4-chlorosulfonyl-2-hydroxy-benzoic acid, in substantially the same manner, as described in Example 1 step g, and was obtained as a white solid, mp 165-167° C.; MS m/e 603 (M−H)+; | Cc1cc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc(C)c1OS(=O)(=O)c1ccc(C(=O)O)c(O)c1 | null | null | null |
1,548,167 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH2:14][OH:15])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11]>CCOC(C)=O.[O-2].[Mn+4].[O-2]>[Cl:1][C:2]1[C:7]([O:8][CH2:9][C:10]([F:12])([F:13])[F:11])=[N:6][CH:5]=[C:4]([CH:3]=1)[CH:14]=[O:15] | OCc1cnc(OCC(F)(F)F)c(Cl)c1 | null | null | [Mn+4] | [O-2] | 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 | 120 | null | To a solution of (5-chloro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methanol (4.00 g, 16.56 mmol) in EtOAc (15 mL) was added manganese(IV) oxide (16.93 g, 166 mmol). The reaction was heated with microwave at 120° C. for 30 minutes. The mixture was then filtered through a pad of celite, and rinsed with EtOAc. The filtrated... | O=Cc1cnc(OCC(F)(F)F)c(Cl)c1 | null | 85.2 | null |
557,531 | ord_dataset-f483e698250b4da0a84f425c7bfa965a | null | 2002-01-01T00:08:00 | true | [F:1][C:2]([F:9])(I)[C:3]([O:5][CH2:6][CH3:7])=[O:4].Br[C:11]1[N:12]=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=1.O.[NH4+].[Cl-]>CS(C)=O.[Cu]>[F:1][C:2]([F:9])([C:11]1[N:12]=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4] | CCOC(=O)C(F)(F)I | Cc1ccc(Br)nn1 | null | [Cu] | [Cl-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | O | null | null | null | null | null | null | null | null | null | null | 0.83 | This procedure is derived from the general method of T. Taguchi, et al. (Tetrahedron Lett., 1986, 27, 6103-6106). Ethyl difluoroiodoacetate (0.355 mL, 651 mg, 2.60 mmol) was added to a rapidly stirred suspension of copper powder (333 mg, 5.24 mmol) in DMSO (6.5 mL) at rt. After 50 min., 3-bromo-6-methylpyridazine (300 ... | CCOC(=O)C(F)(F)c1ccc(C)nn1 | null | 97.1 | null |
1,056,908 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [C:1]([C:3]1[C:4]([O:13][CH2:14][CH2:15][OH:16])=[N:5][NH:6][C:7]=1[N:8]=[CH:9][N:10](C)C)#[N:2].[Cl:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1)N>>[Cl:17][C:18]1[CH:19]=[C:20]([NH:2][C:1]2[N:10]=[CH:9][N:8]=[C:7]3[NH:6][N:5]=[C:4]([O:13][CH2:14][CH2:15][O... | CN(C)C=Nc1[nH]nc(OCCO)c1C#N | Nc1ccc(OCc2ccccn2)c(Cl)c1 | 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 procedure described in Example 1 was repeated using N′-[4-cyano-3-(2-hydroxyethoxy)-1H-pyrazol-5-yl]-N,N-dimethylimidoformamide (1.50 g, 6.72 mmol) and 3-chloro-4-(pyridin-2-ylmethoxy)aniline (1.58 g, 6.72 mmol) to give the title compound as a while solid (2.40 g, 87%); NMR Spectrum: 3.80 (t, 2H), 4.32 (t, 2H), 5.3... | OCCOc1n[nH]c2ncnc(Nc3ccc(OCc4ccccn4)c(Cl)c3)c12 | null | null | null |
376,725 | ord_dataset-846d411edee44814931e062174d7ef12 | null | 1997-01-01T00:09:00 | true | [NH2:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=O)[CH3:10].Cl.[N:13]([O-])=O.[Na+]>O>[F:8][C:6]1[CH:7]=[C:2]2[C:3]([C:9]([CH3:10])=[N:13][NH:1]2)=[CH:4][CH:5]=1 | O=N[O-] | CC(=O)c1ccc(F)cc1N | null | Cl | [Na+] | 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 | -10 | 1 | 1-(2-Amino-4-fluorophenyl)ethanone (9.618 g, 62.9 mmol) was treated with concentrated hydrochloric acid (16 mL) and water (16 mL), and the resulting white suspension was cooled to -10° C. and treated with a solution of sodium nitrite (4.338 g, 62.9 mmol) in 10 mL H2O, maintaining the temperature below 0° C. The resulti... | Cc1n[nH]c2cc(F)ccc12 | null | 32.8 | null |
493,727 | ord_dataset-3f9174c7efcb4f31becbd3516cde9572 | null | 2001-01-01T00:02:00 | true | [Cl:1]N1C(=O)CCC1=O.[S:9]1[C:13]([C:14]2[N:22]3[C:17]([CH2:18][CH2:19][CH2:20][CH2:21]3)=[C:16]([C:23]([NH2:25])=[O:24])[CH:15]=2)=[CH:12][N:11]=[CH:10]1>C(#N)C.C(OCC)C>[Cl:1][C:15]1[C:16]([C:23]([NH2:25])=[O:24])=[C:17]2[N:22]([C:14]=1[C:13]1[S:9][CH:10]=[N:11][CH:12]=1)[CH2:21][CH2:20][CH2:19][CH2:18]2 | O=C1CCC(=O)N1Cl | NC(=O)c1cc(-c2cncs2)n2c1CCCC2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | CC#N | null | null | null | null | null | null | null | null | null | 20 | 2 | N-Chlorosuccinimide is added in 0.05 g portions to a solution of 0.1 g of 3-(5-thiazolyl)-5,6,7,8-tetrahydroindolizine-1-carboxamide in 10 cm3 of acetonitrile at 65° C. After 2 hours a precipitate is seen to form. The mixture is allowed to cool to approximately 20° C., the solid is filtered off and washed with two time... | NC(=O)c1c(Cl)c(-c2cncs2)n2c1CCCC2 | null | null | null |
1,549,271 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [NH:1]1[CH2:4][CH:3]([C:5]2[NH:9][N:8]=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=3)[N:6]=2)[CH2:2]1.[CH3:17][C:18]1[N:19]=[C:20]2[N:25]=[C:24]([C:26]3[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=3)[C:23]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[CH:22][N:21]2[CH:40]=1>>[CH3:17][C:18]1[N:19]=[... | Cc1cccc(-c2n[nH]c(C3CNC3)n2)n1 | Cc1cn2cc(-c3ccccc3)c(-c3ccc(C=O)cc3)nc2n1 | 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 is prepared in analogy to example 37.0. 306 mg 2-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-6-methylpyridine×2HCl (60% pure) are reacted with 200 mg (0.64 mmol) 4-(2-methyl-6-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-benzaldehyde. After the usual work-up and purification 146 mg (42.6%) of the title compound are ob... | Cc1cccc(-c2nc(C3CN(Cc4ccc(-c5nc6nc(C)cn6cc5-c5ccccc5)cc4)C3)n[nH]2)n1 | null | null | null |
830,505 | ord_dataset-47bd90bf5ec74fcd99ce250a56e18c8f | null | 2008-01-01T00:07:00 | true | [C:1]([C:3]1[CH:4]=[C:5]([C:13]([N:15]([CH2:17][C@H:18]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:19][CH:20]=C)[CH3:16])=[O:14])[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2].FC1C=CC([C@H](CC=C)CN(C)C(=[O:54])C2C=C(C(F)(F)F)C=C(C(F)(F)F)C=2)=CC=1>>[C:1]([C:3]1[CH:4]=[C:5]([C:13]([N:15]([CH... | C=CC[C@H](CN(C)C(=O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1)c1ccc(F)cc1 | C=CC[C@H](CN(C)C(=O)c1cc(C#N)cc2ccccc12)c1ccc(F)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 synthesized in an analogous way to that of Method 20b but using 3-cyano-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methyl-1-naphthamide rather than N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (yield, 78%). 1H NMR (400 MHz, CDCl3): 2.4-2.6 (m, 1H), 2.7 (s, 3H), ... | CN(C[C@@H](CC=O)c1ccc(F)cc1)C(=O)c1cc(C#N)cc2ccccc12 | null | null | null |
653,127 | ord_dataset-fe016e2f90e741a590ad77fd5933161f | null | 2004-01-01T00:11:00 | true | [CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH:11]=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[F:22][C:23]([F:47])([F:46])[CH2:24][NH:25][C:26]([C:28]1([CH2:41][CH2:42][CH2:43][CH2:44]Br)[C:40]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[C:34]2[C:29]1=[CH:30][CH:31]=... | O=C(NCC(F)(F)F)C1(CCCCBr)c2ccccc2-c2ccccc21 | COc1ccc(Oc2cccc(N3CCNCC3)n2)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 | Prepared analogously to Example 2 b from 1-[6-(4-methoxy-phenoxy)-pyridin-2-yl]-piperazine and 9-(4-bromo-butyl)-9H-fluorene-9-carboxylic acid-(2,2,2-trifluoroethyl)-amide. | COc1ccc(Oc2cccc(N3CCN(CCCCC4(C(=O)NCC(F)(F)F)c5ccccc5-c5ccccc54)CC3)n2)cc1 | null | null | null |
1,618,860 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)[CH2:4][CH2:3]1.Cl[C:18]1[N:19]=[N:20][C:21]([C:24]2[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=2)=[CH:22][CH:23]=1>>[CH3:29][N:27]1[CH:28]=[C:24]([C:21]2[N:20]=[N:19][C:18]([N:2]3[CH2:7][CH2:6][CH:5]([N:8]4[C:16]5[C:11](=[CH:... | Cn1cc(-c2ccc(Cl)nn2)cn1 | c1ccc2c(c1)ccn2C1CCNCC1 | 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 | The title compound was prepared according to the procedure as described in Example 1, Method B, reacting 1-(piperidin-4-yl)indole HCl salt and 3-chloro-6-(1-methyl-1H-pyrazol-4-yl)pyridazine. | Cn1cc(-c2ccc(N3CCC(n4ccc5ccccc54)CC3)nn2)cn1 | null | null | null |
893,797 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | [CH3:1][C:2]1[C:7](=[O:8])[C@@H:6]([OH:9])[CH2:5][C:4]([CH3:11])([CH3:10])[C:3]=1/[CH:12]=[CH:13]/[C:14](/[CH3:44])=[CH:15]/[CH:16]=[CH:17]/[C:18](/[CH3:43])=[CH:19]/[CH:20]=[CH:21]/[CH:22]=[C:23](\[CH3:42])/[CH:24]=[CH:25]/[CH:26]=[C:27](\[CH3:41])/[CH:28]=[CH:29]/[C:30]1[C:36]([CH3:38])([CH3:37])[CH2:35][C@H:34]([OH:... | CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(=O)[C@@H](O)CC2(C)C)C(C)(C)C[C@H](O)C1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | O | null | null | null | null | null | null | null | null | null | 70 | null | 20 mg analytical grade astaxanthin (97.2 mol % all-trans-astaxanthin and 1.6 mol % 9-cis-astaxanthin and 1.2 mol % 13-cis-astaxanthi) is dissolved in 1 ml pyridine and heated at 70° C. for 30 min. After addition of 8.0 ml cold water, the formed crystals are washed with water and the Raman spectrum shows the presence of... | CC1=C(/C=C/C(C)=C/C=C/C(C)=C\C=C\C=C(C)\C=C\C=C(C)\C=C\C2=C(C)C(=O)[C@@H](O)CC2(C)C)C(C)(C)C[C@H](O)C1=O | null | null | null |
1,094,455 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | C([O:5][C:6](=[O:33])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:21][C:20]=2[NH2:32])[N:15]=1)([CH3:9])[CH3:8])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:32][C:20]1[CH:21]=[C:22]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29]... | CC(C)(C)OC(=O)C(C)(C)Sc1nc(CCOc2ccc(-c3ccc(F)cc3)cc2N)cs1 | 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 | 25 | 12 | 2-[(4-{2-[(3-Amino-4′-fluorobiphenyl-4-yl)oxy]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester (230 mg) obtained in Example 98-1 was dissolved in dichloromethane (2 mL), trifluoroacetic acid (2 mL) was added, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was concen... | CC(C)(Sc1nc(CCOc2ccc(-c3ccc(F)cc3)cc2N)cs1)C(=O)O | null | 72.7 | null |
164,408 | ord_dataset-1385ebf1988241e49636101695ad79e4 | null | 1987-01-01T00:10:00 | true | [NH2:1][CH:2]1[CH2:8][S:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][N:4]([CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:3]1=[O:23].Br[CH:25]([CH2:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>C... | CC(C)(C)OC(=O)CN1CC(c2ccccc2)SCC(N)C1=O | O=C(OCc1ccccc1)C(Br)CCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | 0.34 g of t-butyl α-(6-amino-5-oxo-2-phenylperhydro-1,4-thiazepin-4-yl)acetate [prepared as described in Example 7(g)] was N-alkylated with 0.50 g of benzyl 2-bromo-4-phenylbutyrate in the same manner as in Example 1(h). The reaction product was subjected to silica gel column chromatography using a 1:40 by volume mixtu... | CC(C)(C)OC(=O)CN1CC(c2ccccc2)SCC(NC(CCc2ccccc2)C(=O)OCc2ccccc2)C1=O | null | null | null |
799,396 | ord_dataset-56a22bc0c3b14f87b9aa3f2fc6488ee7 | null | 2007-01-01T00:12:00 | true | [CH2:1]([O:3][C:4](=[O:34])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]2[N:19]([CH2:20][CH2:21][CH3:22])[C:18](=[O:23])[N:17]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)[N:16]=2)=[CH:9][CH:8]=1)[CH3:2].[I:35]I>S([O-])([O-])(=O)=O.[Ag+2].C(O)C>[CH2:1]([O:3][C:4](=[O:34]... | II | CCCn1c(CCc2ccc(OCC(=O)OCC)cc2)nn(-c2ccc(C(F)(F)F)cc2)c1=O | null | [Ag+2] | O=S(=O)([O-])[O-] | 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 | 3.5 | A mixture of (4-{2-[5-Oxo-4-propyl-1-(4-trifluoromethyl-phenyl)-4,5-dihydro-1H-[1,2,4]triazol-3-yl]-ethyl}-phenoxy)acetic acid ethyl ester (180 mg, 0.38 mmol), iodine (105 mg, 0.42 mmol), silver sulfate (131 mg, 0.42 mmol) and ethanol were stirred at room temperature. After 3.5 h, more iodine (86 mg) and silver sulfate... | CCCn1c(CCc2ccc(OCC(=O)OCC)c(I)c2)nn(-c2ccc(C(F)(F)F)cc2)c1=O | null | 94.6 | null |
1,384,070 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]([CH2:15][C:16]2[O:20][C:19]([C:21](OC)=[O:22])=[N:18][N:17]=2)[CH3:14])(=[O:12])=[O:11])=[C:5]([CH3:25])[CH:4]=1.[CH3:26][N:27]([CH3:43])[CH:28]1[CH2:32][CH2:31][N:30]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([CH2:40][NH:41][CH3:42])=[CH:36][CH:35]=2)[CH2:29]1.C[Al... | CNCc1ccc(CN2CCC(N(C)C)C2)cc1 | COC(=O)c1nnc(CN(C)S(=O)(=O)c2c(C)cc(OC)cc2C)o1 | null | C[Al](C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCCl | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared according to general procedure AT using methyl 5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-1,3,4-oxadiazole-2-carboxylate (30 mg, 0.08 mmol), N,N-dimethyl-1-{4-[(methylamino)methyl]benzyl}pyrrolidin-3-amine (32 mg, 0.13 mmol) and trimethylaluminium (2 M in toluene, ... | COc1cc(C)c(S(=O)(=O)N(C)Cc2nnc(C(=O)N(C)Cc3ccc(CN4CCC(N(C)C)C4)cc3)o2)c(C)c1 | null | null | null |
83,674 | ord_dataset-7bed824f566d4af0b51d74d386b14bd6 | null | 1981-01-01T00:07:00 | true | [Br:1]Br.[CH2:3]([CH:10]1[CH2:14][CH2:13][CH2:12][N:11]1[CH3:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+]>[Fe]>[Br:1][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH:10]2[CH2:14][CH2:13][CH2:12][N:11]2[CH3:15])=[CH:5][CH:6]=1 | CN1CCCC1Cc1ccccc1 | BrBr | null | [Fe] | [Na+] | [OH-] | 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 | Add 11.4 moles of bromine at room temperature to 2 g of 2-benzyl-1-methylpyrrolidine and 50 mg of iron powder. Allow the resulting mixture to stand for 2 hours before rendering it alkaline 1 N sodium hydroxide solution. Extract the base with diethyl ether. Distil the ether extract to obtain the title compound as almost... | CN1CCCC1Cc1ccc(Br)cc1 | null | null | null |
168,132 | ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | null | 1988-01-01T00:02:00 | true | [Cl:1][C:2]1[S:10][C:9]2[C:8](=[O:11])[NH:7][CH:6]=[N:5][C:4]=2[CH:3]=1.[Br:12]Br>C(O)(=O)C>[Br:12][C:3]1[C:4]2[N:5]=[CH:6][NH:7][C:8](=[O:11])[C:9]=2[S:10][C:2]=1[Cl:1] | BrBr | O=c1[nH]cnc2cc(Cl)sc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 25 | 2.5 | A solution of 1.12 g (0.006 mole) of 6-chlorothieno[3,2-d]pyrimidin-4(3H)-one and 15 ml of acetic acid at 80° C. was treated with 2.88 g (0.92 ml, 0.018 mole) of bromine. Heating was continued for 2.5 hours during which time solids precipitated. After cooling to room temperature, the mixture was filtered and washed wit... | O=c1[nH]cnc2c(Br)c(Cl)sc12 | null | 43.9 | null |
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