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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,709,957 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [CH3:1][C:2]1[S:6][C:5]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-])=O)=[C:4]([C:17]#[N:18])[CH:3]=1>C(OCC)(=O)C.[Pd]>[NH2:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[NH:7][C:5]1[S:6][C:2]([CH3:1])=[CH:3][C:4]=1[C:17]#[N:18] | Cc1cc(C#N)c(Nc2ccccc2[N+](=O)[O-])s1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of 5-methyl-2-((2-nitrophenyl)amino)thiophene-3-carbonitrile, prepared as described in the previous step, (43.3 g, 0.157 mol) in ethyl acetate (500 mL) was added 10% palladium on carbon (8 g). The black mixture was stirred at room temperature overnight under an atmosphere of hydrogen gas. When LCMS showed... | Cc1cc(C#N)c(Nc2ccccc2N)s1 | null | null | null |
883,117 | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | null | 2009-01-01T00:05:00 | true | [CH3:1][NH:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][N:11]2[CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:7][CH:6]=1)=[O:4].[CH3:20][O:21][C:22]1[C:33]([CH2:34][CH:35]=O)=[CH:32][C:25]2[N:26]([CH3:31])[C:27](=[O:30])[O:28][CH2:29][C:24]=2[CH:23]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C... | COc1cc2c(cc1CC=O)N(C)C(=O)OC2 | CNC(=O)c1ccc2ccn(C3CCNCC3)c2c1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CC(=O)O | null | null | null | null | null | null | null | null | null | 25 | 3 | 80 mg of N-methyl-1-(piperidin-4-yl)-1H-indole-6-carboxamide and 83 mg of (6-methoxy-1-methyl-2-oxo-1,4-dihydro-2H-benz[d][1,3]oxazin-7-yl)acetaldehyde were dissolved in 6 ml of methylene chloride. Thereafter, 0.04 ml of acetic acid and 99 mg of sodium triacetoxyborohydride were added to the reaction solution, and the ... | CNC(=O)c1ccc2ccn(C3CCN(CCc4cc5c(cc4OC)COC(=O)N5C)CC3)c2c1 | null | 95.2 | null |
222,529 | ord_dataset-59f453c3a3d34a89bfd97b6b8b151908 | null | 1991-01-01T00:02:00 | true | [NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[N:9][C:4]=2[N:3]=[CH:2]1.Cl[CH2:11][C:12]1[CH:30]=[CH:29][C:15]([C:16]([N:18]([CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:17])=[CH:14][N:13]=1>CC(N(C)C)=O>[CH:24]1([N:18]([CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23]2)[C:16]([C:15]2[CH:14]=[N:13][... | O=C(c1ccc(CCl)nc1)N(C1CCCC1)C1CCCC1 | c1cnc2nc[nH]c2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)N(C)C | null | null | null | null | null | null | null | null | null | null | 25 | 60 | To a stirred solution of imidazopyridine (540 mg, 4.5 mmol) in dimethylacetamide (100 mL) under argon, the product of Example D (1.6 g,) was added in one portion. The reaction temperature was slowly raised to 80°-85° C. and was stirred for 60 h. The reaction flask was cooled to room temperature and the solvent was remo... | O=C(c1ccc(Cn2ccc3ncnc-3c2)nc1)N(C1CCCC1)C1CCCC1 | null | null | null |
291,224 | ord_dataset-6c3ec086c8c9475e8d31a44641b49e02 | null | 1994-01-01T00:06:00 | true | [CH2:1]([O:11][C:12]1[CH:35]=[CH:34][C:15]([C:16]([NH:18][C:19]2[CH:24]=[C:23]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:22]=[CH:21][C:20]=2[OH:33])=O)=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClC1C=CC=CC=1Cl>[CH2:1]([O:11]... | CCCCCCCCCCOc1ccc(C(=O)Nc2cc(CCCCCCCC)ccc2O)cc1 | null | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | Clc1ccccc1Cl | null | null | null | null | null | null | null | null | null | null | 0.62 | In a 30 ml-round-bottomed flask, 1.00 g (2.08 mM) of 2-(4-decyloxybenzoylamino)-4-octylphenol, 0.07 g (0.68 mM) of p-toluenesulfonic acid monohydrate and 10 ml of o-dichlorobenzene were placed, followed by stirring for 37 min. at 188°-193° C. After the reaction, o-dichlorobenzene was distilled off under reduced pressur... | CCCCCCCCCCOc1ccc(-c2nc3cc(CCCCCCCC)ccc3o2)cc1 | null | 61.3 | null |
1,647,354 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | C([Si](C)(C)[O:6][CH2:7][C:8]([N:11]1[C:19]2[C:18]([F:20])=[CH:17][N:16]=[CH:15][C:14]=2[C:13]([C:21]([C:23]2[CH:24]=[C:25]([NH:29][C:30](=[O:42])[CH2:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=3)[CH:26]=[N:27][CH:28]=2)=[O:22])=[CH:12]1)([CH3:10])[CH3:9])(C)(C)C>C1COCC1>[F:20][C:18]1[... | CC(C)(CO[Si](C)(C)C(C)(C)C)n1cc(C(=O)c2cncc(NC(=O)Cc3ccc(C(F)(F)F)cc3)c2)c2cncc(F)c21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 2 | To a solution of N-(5-{1-[2-(tert-Butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-7-fluoro-1H-pyrrolo[3,2-c]pyridine-3-carbonyl}-pyridin-3-yl)-2-(4-trifluoromethyl-phenyl)-acetamide (Preparation 1, 45 mg, 49 μmol) in THF (5 mL) 4M dioxane-HCl (0.5 mL) was added and stirred at room temperature for 2 hours. The reaction w... | CC(C)(CO)n1cc(C(=O)c2cncc(NC(=O)Cc3ccc(C(F)(F)F)cc3)c2)c2cncc(F)c21 | null | 83 | null |
1,510,555 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | [Na].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(O)C.O>[CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])([C:2]([O:10][CH2:11][CH3:12])=[O:9])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16] | CCOC(=O)CCl | CCOC(=O)CC(=O)OCC | null | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | 15 | null | Sodium metal (23 gram, 1 mole) was dissolved in dry ethanol (500 ml) with stirring. To this 160 gram (1 mole) of diethyl malonate (compound [2]) was added in 30 minutes. The reaction mixture was cooled to 15° C. and ethyl chloroacetate (compound [1], 117 gm, 0.095 mole) was then added drop wise in 30 minutes. On comple... | CCOC(=O)CC(C(=O)OCC)C(=O)OCC | null | null | null |
1,268,847 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | C([O:8][N:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[C:24](=[O:25])[C:23]2[CH2:26][CH2:27][CH:28]=[CH:29][C:22]=2[O:21][C:20]2[CH:30]=[CH:31][CH:32]=[CH:33][C:19]1=2)[CH:10]=[O:11])C1C=CC=CC=1.[H][H]>CO.[Pd]>[OH:8][N:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[C:24](=[O:25])[C:23]2[CH:26]... | [H][H] | O=CN(CCCCCCN1C(=O)C2=C(C=CCC2)Oc2ccccc21)OCc1ccccc1 | 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 | null | Title compound 403 (348 mg, 0.783 mmol) was dissolved in methanol (10 mL). The 10% palladium on charcoal (120 mg, 33% by wt) was added. The reaction mixture was stirred for 3 hours under 1 atmosphere of hydrogen at room temperature. The reaction mixture was filtered to remove the catalyst and the filtrate was evaporate... | O=CN(O)CCCCCCN1C(=O)c2ccccc2Oc2ccccc21 | null | 6.5 | null |
1,712,201 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [Cl:1][C:2]1[C:3]([N:11]2[CH:21]=[C:14]3[C:15](Cl)=[N:16][CH:17]=[C:18]([F:19])[C:13]3=[N:12]2)=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[C:5]#[N:6].[Br:22][Si](C)(C)C>C(#N)CC>[Br:22][C:15]1[C:14]2=[CH:21][N:11]([C:3]3[C:2]([Cl:1])=[CH:9][C:8]([F:10])=[CH:7][C:4]=3[C:5]#[N:6])[N:12]=[C:13]2[C:18]([F:19])=[CH:17][N:16]=1 | C[Si](C)(C)Br | N#Cc1cc(F)cc(Cl)c1-n1cc2c(Cl)ncc(F)c2n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCC#N | null | null | null | null | null | null | null | null | null | null | 80 | null | 3-Chloro-2-(4-chloro-7-fluoropyrazolo[4,3-c]pyridin-2-yl)-5-fluorobenzonitrile (735 mg, 2.26 mmol) was suspended in propionitrile (44 mL), under an atmosphere of nitrogen and bromotrimethylsilane (0.82 mL, 5.64 mmol) was added. The reaction mixture was heated at 80° C. for 5 hours. The resultant mixture was cooled to r... | N#Cc1cc(F)cc(Cl)c1-n1cc2c(Br)ncc(F)c2n1 | null | 99.9 | null |
1,696,846 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[F:18])[O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][OH:13])=[CH:8][C:7]=1[F:14].Cl[C:20]1[CH:36]=[C:24]2[N:25](C(OC(C)(C)C)=O)[CH2:26][CH2:27][CH2:28][N:23]2[C:22](=[O:37])[N:21]=1>>[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[F:18])[O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][... | OCc1ccc(Oc2ccc(F)c(F)c2)c(F)c1 | CC(C)(C)OC(=O)N1CCCn2c1cc(Cl)nc2=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 or its salt was prepared by a procedure similar to that described for E111 starting from (4-(3,4-difluorophenoxy)-3-fluorophenyl)methanol and tert-butyl 8-chloro-6-oxo-2,3,4,6-tetrahydro-1H-pyrimido[1,6-a]pyrimidine-1-carboxylate. | O=c1nc(OCc2ccc(Oc3ccc(F)c(F)c3)c(F)c2)cc2n1CCCN2 | null | null | null |
1,181,011 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | [OH:1][C@H:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.[N:7]([C:10]1[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[N:14][CH:15]=1)=[C:8]=[S:9]>>[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:8](=[S:9])[NH:7][C:10]2[CH:15]=[N:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH2:3]1 | COc1ccc(N=C=S)cn1 | O[C@H]1CCNC1 | null | null | null | null | null | null | null | 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 (S)-3-hydroxypyrrolidine and 5-isothiocyanato-2-methoxypyridine (J. Org. Chem. (1980), 45, 4219), using the same method as that described for preparation 35, in 99% yield. 1H NMR (400 MHz, CD3OD) δ: 1.91-2.22 (m, 2H), 3.69-3.81 (m, 4H), 3.88 (s, 3H), 4.40-4.52 (m, 1H), 6.78 (d, 1H),... | COc1ccc(NC(=S)N2CC[C@H](O)C2)cn1 | null | 99 | null |
278,953 | ord_dataset-140fb5527ff24f97bcf0094c5d100120 | null | 1993-01-01T00:11:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:17]([CH2:18][CH:19]3[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][C:27]4[CH:32]=[CH:31][C:30]([O:33]C)=[CH:29][CH:28]=4)[CH2:21][CH2:20]3)=[N:16][C:15]3[C:10]2=[N:11][CH:12]=[N:13][C:14]=3[OH:35])=[CH:4][CH:3]=1.Br>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:17]([CH2:18][CH:1... | COc1ccc(CCN2CCC(Cc3nc4c(O)ncnc4n3Cc3ccc(F)cc3)CC2)cc1 | null | null | Br | 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 | 80 | 4 | A mixture of 2.7 parts of 9-[(4-fluorophenyl)methyl]-8-[[1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]-methyl]-9H-purin-6-ol and 75 parts of a hydrobromic acid solution 48% in water was stirred for 4 hours at 80° C. After evaporation, the residue was taken up in water and treated with sodium carbonate. The product was ex... | Oc1ccc(CCN2CCC(Cc3nc4c(O)ncnc4n3Cc3ccc(F)cc3)CC2)cc1 | null | 38.6 | null |
541,749 | ord_dataset-49124ff635234889bd8dcfe87f4f9013 | null | 2002-01-01T00:04:00 | true | [Li].Br[C:3]1(Br)[CH2:8][CH:7]=[CH:6][CH:5]=[C:4]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Si:16](Cl)(Cl)([Cl:18])[Cl:17]>CCCCC.CCOCC>[Cl:17][Si:16]1([Cl:18])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:4]2[C:3]1=[CH:8][CH:7]=[CH:6][CH:5]=2 | Cl[Si](Cl)(Cl)Cl | BrC1(Br)CC=CC=C1c1ccccc1 | null | [Li] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | CCCCC | null | null | null | null | null | null | null | null | null | null | null | Lithium wire (3.33 g, 0.08 mol) was washed with pentane, carefully cut into small pieces, and suspended in 150 mL of Et2O. While stirring, 2,2-dibromobiphenyl (25 g, 0.08 mol) 100 mL of diethyl ether was added dropwise over 1 hour and the contents were allowed to stir for 10 hours. The mixture was filtered through a fr... | Cl[Si]1(Cl)c2ccccc2-c2ccccc21 | null | null | null |
1,058,133 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | C([CH:4]([CH2:12][CH2:13][CH2:14]C)[CH:5]([OH:11])[CH2:6][C:7]([O:9][CH3:10])=[O:8])C=C.[CH2:16](C(CC=C)C=O)[CH:17]([CH3:19])[CH3:18]>>[OH:11][CH:5]([CH2:4][CH2:12][CH:13]=[CH2:14])[CH:6]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:7]([O:9][CH3:10])=[O:8] | C=CCC(CCCC)C(O)CC(=O)OC | C=CCC(C=O)CC(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The compound of interest (4.5 g, 61%) was obtained as an oil substance (diastereomeric mixture) in the same way as in paragraph (10-a) using 2-isobutyl-4-pentenal. | C=CCCC(O)C(CC(C)C)C(=O)OC | null | null | null |
1,289,378 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | CS(O[CH2:6][CH2:7][N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[N:10]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[C:9]1=[O:30])(=O)=O.[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>ClCCl>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([N:10]2[C@@H:11]([C:13]3[CH:18... | C1COCCN1 | CS(=O)(=O)OCCN1C[C@H](c2cccc(C(F)(F)F)c2)N(c2ccc(Cl)cc2)C1=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 | 3 | To a solution of (S)-2-(3-(4-chlorophenyl)-2-oxo-4-(3-(trifluoromethyl)phenyl)imidazolidin-1-yl)ethyl methanesulfonate (30 mg, 0.065 mmol) in anhydrous dichloromethane (3 mL) is added morpholine (16.9 mg, 0.194 mmol). After 3 h at room temperature, the residue is purified by preparatory LC/MS to provide the title compo... | O=C1N(CCN2CCOCC2)C[C@H](c2cccc(C(F)(F)F)c2)N1c1ccc(Cl)cc1 | null | null | null |
455,419 | ord_dataset-4a5b4fffffb34daa876fff1f127a4135 | null | 2000-01-01T00:01:00 | true | [CH3:1][CH:2]([O:4][C:5]([C:7]1[N:11]=[C:10]([C@H:12]([N:24]([C:26](=[O:47])[C@H:27]([NH:39]C(OC(C)(C)C)=O)[CH2:28][C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=2)[CH3:25])[CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[O:9][N:8]=1)=[O:6])[CH3:3].FC... | CC(C)OC(=O)c1noc([C@@H](Cc2ccc3ccccc3c2)N(C)C(=O)[C@@H](Cc2ccc3ccccc3c2)NC(=O)OC(C)(C)C)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | null | 0.17 | 5-{(1R)-1-[N-((2R)-2-tert-Butoxycarbonylamino-3-(2-naphthyl)propionyl)-N-methylamino]-2-(2-naphthyl)ethyl}-[1,2,4]oxadiazole-3-carboxylic acid (2-propyl)ester (2.1 g, 3.3 mmol) was suspended in a saturated mixture of trifluoroacetic acid and dichloromethane (1:1, 60 ml). After 10 min at 20° C., the reaction mixture was... | CC(C)OC(=O)c1noc([C@@H](Cc2ccc3ccccc3c2)N(C)C(=O)[C@H](N)Cc2ccc3ccccc3c2)n1 | null | 124.2 | null |
506,708 | ord_dataset-631d58dab387485c8eb0db4c20a232b7 | null | 2001-01-01T00:06:00 | true | [C:1]1([C:7]2[S:8][C:9]([CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:18]([C@@H:20]1[C@@H:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:23][N:22]([C@H:31]([CH:44]2[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]2)[C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][C:... | COc1ccc(COC(=O)[C@@H](C2CCCCC2)N2C[C@H](c3ccccc3)[C@@H](C=O)C2)cc1 | c1ccc(-c2ncc(C3CCNCC3)s2)cc1 | 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 12 mg of 4-(2-phenyl-thiazol-5-yl)-piperidine (from Step B) in 3 ml of DCE was added 35 mg of a-(R)-(3-(R)-formyl4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid, p-methoxybenzyl ester (prepared above as Aldehyde 5) followed by 19 mg of sodium triacetoxyborohydride. The reaction was stirred overnight at room temp... | COc1ccc(COC(=O)[C@@H](C2CCCCC2)N2C[C@H](CN3CCC(c4cnc(-c5ccccc5)s4)CC3)[C@@H](c3ccccc3)C2)cc1 | null | 85.9 | null |
25,457 | ord_dataset-2ada3fda46fc44719ba0c8001f53c1b3 | null | 1977-01-01T00:06:00 | true | [NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[NH:5][C:6](=[O:9])[CH2:7][CH3:8].C([O-])(=O)C.[Na+].[CH:18]1([C:21](Cl)=[O:22])[CH2:20][CH2:19]1.[Cl-]>C(O)(=O)C>[C:6]([NH:5][C:4]1[CH:3]=[C:2]([CH:12]=[CH:11][CH:10]=1)[NH:1][C:21]([CH:18]1[CH2:20][CH2:19]1)=[O:22])(=[O:9])[CH2:7][CH3:8] | O=C(Cl)C1CC1 | CCC(=O)Nc1cccc(N)c1 | null | CC(=O)[O-] | [Cl-] | [Na+] | 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 | null | Meta-aminopropionanilide, 13.1 g. (0.08 mole) is dissolved in 200 ml. of a 50/50 v/v mixture of glacial acetic acid and saturated sodium acetate solution. To this solution is added 9.2 g. (0.088 moles) of cyclopropane carbonyl chloride. The chloride is added slowly with adequate stirring and cooling. The product, which... | CCC(=O)Nc1cccc(NC(=O)C2CC2)c1 | null | null | null |
838,313 | ord_dataset-074f86301ec5441ab3b52d902ac06949 | null | 2008-01-01T00:09:00 | true | [NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])=[O:9])=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.FC(F)(F)C(O)=O.[CH3:25][S:26]([N:29]1[CH2:34][CH2:33][CH:32]([NH2:35])[CH2:31][CH2:30]1)(=[O:28])=[O:27]>>[NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])=[O:9])=[CH:6][CH:5]=[... | Nc1nc(Cl)ccc1C(=O)c1ccccc1F | CS(=O)(=O)N1CCC(N)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from (2-Amino-6-chloro-pyridin-3-yl)-(2-fluoro-phenyl)-methanone (Example 7) and 1-methanesulfonyl-piperidin-4-ylamine (Step A, Example 6) using the procedure described in Step B. Example 6. HRMS, observed: 392.1329, calcd for M+: 392.1318. | CS(=O)(=O)N1CCC(Nc2ccc(C(=O)c3ccccc3F)c(N)n2)CC1 | null | null | null |
967,398 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]([S:14]([N:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][C@@H:18]3[CH3:30])(=[O:16])=[O:15])[CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:4][N:3]=1.[F:31][C:32]1[CH:33]=[C:34]([CH2:38][CH2:39][NH2:40])[CH:35]=[CH:36][CH:37]=1>>[F:31][C:32]1[CH:33]=[C:34]([CH:35]=[CH:36][CH:37]=1)[CH2:3... | C[C@H]1CN(C(=O)OC(C)(C)C)CCN1S(=O)(=O)c1cccc(-c2ccnc(Cl)n2)c1 | NCCc1cccc(F)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 | Intermediate 153 from above was coupled with 2-(3-fluorophenyl)ethanamine following procedure F. The product was deprotected by procedure G2. LC-MS showed the product had the expected M+H+ of 456. 1H NMR (Varian 300 MHz, MeOD-d6, shifts relative to the solvent peak at 3.31 ppm) δ 8.6 (d, 1H) 8.5 (d, 1H) 8.4 (d, 1H), 8.... | C[C@H]1CNCCN1S(=O)(=O)c1cccc(-c2ccnc(NCCc3cccc(F)c3)n2)c1 | null | null | null |
1,767,705 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [NH2:1][CH2:2][C@@H:3]1[C@H:8]([CH3:9])[CH2:7][CH2:6][CH2:5][N:4]1[C:10]([C:12]1[C:17]([N:18]2[N:22]=[CH:21][CH:20]=[N:19]2)=[CH:16][CH:15]=[CH:14][C:13]=1[F:23])=[O:11].Br[C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][N:26]=1>>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([NH:1][CH2:2][C@@H:3]2[C@H:8]([CH3:9])[CH2:7][CH2:6][CH2:... | Clc1ccc(Br)nc1 | C[C@@H]1CCCN(C(=O)c2c(F)cccc2-n2nccn2)[C@@H]1CN | null | null | null | null | null | null | null | 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 following the same general protocol as described for Example A1 using ((2S,3R)-2-(aminomethyl)-3-methylpiperidin-1-yl)(2-fluoro-6-(2H-1,2,3-triazol-2-yl)phenyl)methanone and 2-bromo-5-chloropyridine. ESI-MS (m/z): 429 [M+1]+. | C[C@@H]1CCCN(C(=O)c2c(F)cccc2-n2nccn2)[C@@H]1CNc1ccc(Cl)cn1 | null | null | null |
69,380 | ord_dataset-cb0fdfa937234c78b020ec878a93b94c | null | 1980-01-01T00:08:00 | true | [F:1][C:2]([F:24])([F:23])[C:3]([C:9]1[CH:10]=[C:11]2[C:16]3=[C:17]([CH2:19][CH2:20][N:15]3[C:14](=[O:21])[CH:13]=[C:12]2[CH3:22])[CH:18]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].[CH3:25]N(C)C=O.CC(C)([O-])C.[K+].S(OC)(OC)(=O)=O>O>[F:5][C:4]([F:7])([F:6])[C:3]([C:9]1[CH:10]=[C:11]2[C:16]3=[C:17]([CH2:19][CH2:20][N:15]3[C:14]... | Cc1cc(=O)n2c3c(cc(C(O)(C(F)(F)F)C(F)(F)F)cc13)CC2 | CN(C)C=O | null | CC(C)(C)[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | COS(=O)(=O)OC | null | null | null | null | null | null | null | null | null | 25 | null | To a stirred mixture of 3.5 g of 1,2-dihydro-8-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-6-methyl-4H-pyrrolo[3,2,1-ij]quinolin-4-one and 20 ml of dry dimethylformamide is added 1.3 g (0.012 mole) of potassium tert-butoxide in a dry nitrogen atmosphere. The mixture is heated gently to 100° and is allowed to c... | COC(c1cc2c3c(c1)c(C)cc(=O)n3CC2)(C(F)(F)F)C(F)(F)F | null | 49 | null |
710,344 | ord_dataset-c8069773c1a148aca8ab417108daacc5 | null | 2006-01-01T00:05:00 | true | [N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH2:9][C:10](=[O:16])[NH:11]3)=[CH:3][CH:2]=1.[CH3:17][C:18]1[CH:22]=[C:21]([CH3:23])[NH:20][C:19]=1[CH:24]=O>>[CH3:17][C:18]1[CH:22]=[C:21]([CH3:23])[NH:20][C:19]=1[CH:24]=[C:9]1[C:8]2[C:12](=[CH:13][CH:14]=[CH:15][C:7]=2[C:4]2[CH:5]=[CH:6][N:1]=[CH:... | Cc1cc(C)c(C=O)[nH]1 | O=C1Cc2c(cccc2-c2ccncc2)N1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 4-Pyridin-4-yl-1,3-dihydroindol-2-one was condensed with 3,5-dimethyl-1H-pyrrole-2-carbaldehyde to give the title compound. | Cc1cc(C)c(C=C2C(=O)Nc3cccc(-c4ccncc4)c32)[nH]1 | null | null | null |
1,628,588 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [NH2:1][CH2:2][CH2:3][N:4]([CH2:17][CH3:18])[CH2:5][CH2:6][O:7][C:8]1[C:9]([N+:14]([O-:16])=[O:15])=[N:10][CH:11]=[CH:12][CH:13]=1.C(N(CCN[C:35]([C:37]1[CH:46]=[N:45][C:44]2[C:39](=[CH:40][CH:41]=[C:42]([I:47])[CH:43]=2)[N:38]=1)=[O:36])CCOC1C(F)=NC=CC=1)C>>[CH2:17]([N:4]([CH2:3][CH2:2][NH:1][C:35]([C:37]1[CH:46]=[N:45... | CCN(CCN)CCOc1cccnc1[N+](=O)[O-] | CCN(CCNC(=O)c1cnc2cc(I)ccc2n1)CCOc1cccnc1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This compound was prepared, starting from compound 59 (600 mg, 2.36 mmol), according to the procedure developed for compound 10. Reaction time under reflux: 12 h; the purification was performed using column chromatography (Al2O3, CH2C2/EtOH, 99/1, v/v) to give compound 60 (902 mg, 1.68 mmol) as a light sensitive brown ... | CCN(CCNC(=O)c1cnc2cc(I)ccc2n1)CCOc1cccnc1[N+](=O)[O-] | null | 71 | null |
1,086,200 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([C@@H:14]([NH:16]C(=O)OC(C)(C)C)[CH3:15])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[ClH:24]>O1CCOCC1.CO>[ClH:24].[ClH:24].[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([C@@H:14]([NH2:16])[CH3:15])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1 | C[C@H](NC(=O)OC(C)(C)C)c1ccc(N2CCN(C)CC2)cc1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | CO | null | null | null | null | null | null | null | null | null | 25 | null | A solution of 1,1-dimethylethyl {(1S)-1-[4-(4-methylpiperazin-1-yl)phenyl]ethyl}carbamate (2 g, 6.3 mmol) and 4N hydrogen chloride in dioxane (5 mL) in methanol (5 mL) was refluxed for 2 min. After cooling to room temperature the mixture was concentrated and rotary evaporated from benzene, and further dried in vacuo to... | C[C@H](N)c1ccc(N2CCN(C)CC2)cc1 | null | 95 | null |
1,334,687 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [CH3:1][C:2]1[NH:6][N:5]=[C:4]([NH2:7])[CH:3]=1.[C:8]1(=O)[O:13][C:11](=[O:12])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]12>O1CCOCC1>[CH3:1][C:2]1[NH:6][N:5]=[C:4]([N:7]2[C:11](=[O:12])[C:10]3[C:9](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8]2=[O:13])[CH:3]=1 | O=C1OC(=O)c2ccccc21 | Cc1cc(N)n[nH]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | In a 100 mL round-bottom flask a mixture of 5-methyl-1H-pyrazol-3-amine (Aldrich, 500 mg, 5.15 mmol) and phthalic anhydride (ALDRICH) (1.07 g, 7.21 mmol) in 1,4-dioxane (30 mL) was stirred at reflux for 25 hours. Reaction was allowed to reach room temperature and the formed precipitate was filtered and washed with EtOH... | Cc1cc(N2C(=O)c3ccccc3C2=O)n[nH]1 | null | 50.3 | null |
281,168 | ord_dataset-1953a9402dda47b6bcfe3e3cb9ab8a07 | null | 1993-01-01T00:12:00 | true | [CH2:1]([C:4]1[CH:5]=[C:6]([N+:10]([O-])=O)[CH:7]=[CH:8][CH:9]=1)[CH:2]=[CH2:3]>C(OCC)(=O)C.[Pd]>[CH2:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[NH2:10])[CH2:2][CH3:3] | C=CCc1cccc([N+](=O)[O-])c1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | 2 | To a suspension of ethyltriphenylphosphonium bromide (22 g) in tetrahydrofuran (150 ml) at -78° C. was added dropwise a solution of n-butyllithium in hexane (59.3 mmol). The mixture was left to warm to room temperature over 30 minutes, then cooled to -78° C. and a solution of 3-nitrobenzaldehyde (7.5 g) in tetrahydrofu... | CCCc1cccc(N)c1 | null | 99.5 | null |
2,028 | ord_dataset-a0bc986c3cf848c2a1ea93b297d1ad89 | null | 1976-01-01T00:02:00 | true | [CH3:1][CH:2]([CH3:8])[CH2:3][CH2:4][C:5](=[O:7])[CH3:6].[CH2:9](O)[CH:10]=[CH:11][CH2:12][OH:13].C1CCCCC1>C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C1(C=CC(O)=CC=1)O.O>[CH2:4]([C:5]1([CH3:6])[O:13][CH2:12][CH:11]=[CH:10][CH2:9][O:7]1)[CH2:3][CH:2]([CH3:8])[CH3:1] | CC(=O)CCC(C)C | OCC=CCO | null | O=C(O)CC(O)(CC(=O)O)C(=O)O | Oc1ccc(O)cc1 | 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 | 25 | null | To a one liter flask equipped with heating jacket, agitator and condenser fitted with a Dean-Stark trap was charged 136 grams (1.2 mole) 5-methyl-2-hexanone, 88 grams (1.0 mole) 2-butene-1,4-diol, 160 grams cyclohexane, 2 grams citric acid and 0.3 grams hydroquinone. The mixture was heated with vigorous agitation at re... | CC(C)CCC1(C)OCC=CCO1 | null | 82.5 | null |
764,710 | ord_dataset-7a8649d55889427e85b208ae89475895 | null | 2007-01-01T00:04:00 | true | [C:1]([OH:20])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[OH:21][CH2:22][CH2:23][NH:24][CH2:25][CH2:26][NH2:27]>>[C:1]([NH:27][CH2:26][CH2:25][NH:24][CH2:23][CH2:22][OH:21])(=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8... | NCCNCCO | CCCCCCCCCCCCCCCCCC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The dehydration condensation reaction of stearic acid with N-hydroxyethyl ethylene diamine was carried out, and the reaction product was hydrolyzed and distilled to give N-stearoyl-N′-hydroxyethyl ethylene diamine. It was dissolved in ethanol, and 1.1-fold equivalents (based on the amine) of formalin was added dropwise... | CCCCCCCCCCCCCCCCCC(=O)NCCNCCO | null | null | null |
1,539,946 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | C(N(C(C)C)CC)(C)C.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].[C:33](Cl)(=[O:36])[CH:34]=[CH2:35]>C1COCC1>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([S:23]([C:26]2[CH:31]... | C=CC(=O)Cl | CC(C)(C)OC(=O)N1CCC(S(=O)(=O)c2ccc(N)cc2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 1 | Diisopropylethylamine (0.09 ml, 0.5 mmol) was added in one portion to a stirred solution of 4-(4-Amino-benzenesulfonyl)-piperidine-1-carboxylic acid tert-butyl ester (0.11 g, 0.33 mmol) in THF (3 ml) at room temperature. To this mixture was added acryloyl chloride (0.03 ml, 0.5 mmol) in one portion and the mixture was ... | C=CC(=O)Nc1ccc(S(=O)(=O)C2CCN(C(=O)OC(C)(C)C)CC2)cc1 | null | 15.4 | null |
1,645,597 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | [O:1]=[S:2]1(=[O:40])[CH2:6][CH2:5][CH:4]=[C:3]1[C:7]1[CH:39]=[CH:38][C:10]2[NH:11][C:12]([C:17]3[C:18](=[O:37])[N:19]([CH2:29][C:30]4[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=4)[C@@H:20]4[C@H:25]([C:26]=3[OH:27])[C@@H:24]3[CH2:28][C@H:21]4[CH2:22][CH2:23]3)=[N:13][S:14](=[O:16])(=[O:15])[C:9]=2[CH:8]=1>CO.[Pd]>[O:4... | O=C1C(C2=NS(=O)(=O)c3cc(C4=CCCS4(=O)=O)ccc3N2)=C(O)[C@@H]2[C@H]3CC[C@H](C3)[C@@H]2N1Cc1ccc(F)cc1 | 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 | 25 | 16 | (1R,2S,7R,8S)-5-[7-(1,1-Dioxo-4,5-dihydro-1H-1λ6-thiophen-2-yl)-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl]-3-(4-fluoro-benzyl)-6-hydroxy-3-aza-tricyclo[6.2.1.02,7]undec-5-en-4-one (prepared as described in Example 20, 30 mg, 0.05 mmol) was dissolved in methanol (15 mL) and 5% palladium on charcoal (100 mg) ... | O=C1C(C2=NS(=O)(=O)c3cc(C4CCCS4(=O)=O)ccc3N2)=C(O)[C@@H]2[C@H]3CC[C@H](C3)[C@@H]2N1Cc1ccc(F)cc1 | null | 88 | null |
448,566 | ord_dataset-a4f0b79f6b9847168861270b79f84afa | null | 1999-01-01T00:11:00 | true | Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[CH:22]=[C:21]([OH:25])[CH:20]=[CH:19][C:18]=2[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][C@@H:16]2[F:26])([CH3:14])[C:12](=[O:27])[CH2:11][CH2:10]1.[I-:28].[Na+].O>CC(CC)=O>[F:26][C@H:16]1[CH2:15][C@@:13]2([CH3:14])[C@@H:9]([CH2:10][CH2:11][C:12]2=[O:27])[C... | [I-] | C[C@]12C[C@H](F)[C@@H]3c4ccc(O)cc4C[C@@H](CCCCCCl)[C@H]3[C@@H]1CCC2=O | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCC(C)=O | O | null | null | null | null | null | null | null | null | null | 90 | 8 | 5.0 g of 7α-(5-chloropentyl)-11β-fluoro-3-hydroxy-estra-1,3,5(10)-trien-17-one is dissolved in 80 ml of ethyl methyl ketone, mixed with 5.7 g of sodium iodide and stirred overnight at a bath temperature of 90° C. For working-up, the reaction mixture is cooled to room temperature, stirred into water, extracted 3 times w... | C[C@]12C[C@H](F)[C@@H]3c4ccc(O)cc4C[C@@H](CCCCCI)[C@H]3[C@@H]1CCC2=O | null | 110.3 | null |
213,539 | ord_dataset-b67d30cd146f49dcbf24faee022f1a09 | null | 1990-01-01T00:08:00 | true | [CH2:1]([SH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Na].[CH3:15][C:16]1([CH3:63])[CH2:21][CH:20]([N:22]([C:33]2[N:38]=[C:37]([N:39]([CH:50]3[CH2:55][C:54]([CH3:57])([CH3:56])[NH:53][C:52]([CH3:59])([CH3:58])[CH2:51]3)[CH:40]3[CH2:45][C:44]([CH3:47])([CH3:46])[NH:43][C:42]([... | CCCCCCCCCCCCS | CC1(C)CC(N(c2nc(Cl)nc(N(C3CC(C)(C)NC(C)(C)C3)C3CC(C)(C)NC(C)(C)C3)n2)C2CC(C)(C)NC(C)(C)C2)CC(C)(C)N1 | null | [Na] | 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 | null | null | Following the procedure described in Example 11 and using 20.3 g (0.11 mol) of 1-dodecanthiol, 2.53 g (0.11 mol) of sodium and 70.25 g (0.1 mol) of 2,4-bis[N,N-bis(2,2,6,6-tetramethyl-4-piperidyl)amino]-6-chloro-1,3,5-triazine in 250 ml of xylene, the product of melting point 168°-170° C. is obtained. | CCCCCCCCCCCCSc1nc(N(C2CC(C)(C)NC(C)(C)C2)C2CC(C)(C)NC(C)(C)C2)nc(N(C2CC(C)(C)NC(C)(C)C2)C2CC(C)(C)NC(C)(C)C2)n1 | null | null | null |
526,417 | ord_dataset-293186f5c9b441cab57f03cd3a18ac26 | null | 2001-01-01T00:11:00 | true | Cl[C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:14])[CH:8]=2)[N:3]=1.[NH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=1.CO.N.C(Cl)Cl>>[Cl:28][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][C:24]=1[Cl:27])[CH2:20][NH:19][CH2:18][CH2:17][CH2:16][... | NCCCNCc1ccc(Cl)c(Cl)c1 | COc1cc(Cl)nc2ccc(C)cc12 | null | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CO | null | null | null | null | null | null | null | null | null | 100 | 15 | A mixture of 2-chloro-4-methoxy-6-methylquinoline (94 mg, 0.45 mmol) and N-(3-aminoprop-1-yl)-3,4-dichlorobenzylamine (0.21 g) was heated at 70° C. for 15 h, at 100° C. for 2 h, and then at 120° C. for 15 h. The resulting mixture was submitted to column chromatography (silica gel, MeOH:NH3:CH2Cl2 20:2:100) to give the ... | COc1cc(NCCCNCc2ccc(Cl)c(Cl)c2)nc2ccc(C)cc12 | null | null | null |
1,021,770 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:11]([CH2:16][OH:17])=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]>C(Cl)Cl.O=[Mn]=O>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:11]([CH:16]=[O:17])=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2] | O=[N+]([O-])c1cccc(-c2cccnc2CO)c1 | null | null | O=[Mn]=O | 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 | 48 | To a stirred solution of [3-(3-nitrophenyl)-pyridin-2-yl]-methanol (69 mg, 0.30 mmol) (Agrawal, K. C. et al. J. Med. Chem. 1974, 17, 631-5) in dry CH2Cl2 (5 mL) was added activated MnO2 (90% purity, <10 micron, 251 mg, 2.89 mmol). The resulting heterogeneous mixture was stirred 2 d, at which point the black slurry was ... | O=Cc1ncccc1-c1cccc([N+](=O)[O-])c1 | null | 96.4 | null |
1,678,493 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | C([O:3][C:4]([C:6]1[N:10]([CH3:11])[N:9]=[CH:8][C:7]=1[C:12]1[CH:43]=[CH:42][C:15]([C:16]([N:18]([C@@H:29]2[CH2:34][CH2:33][CH2:32][N:31]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:30]2)[C:19]2[N:20]=[CH:21][CH:22]=[C:23]3[CH:27]=[CH:26][N:25]([CH3:28])[C:24]=23)=[O:17])=[CH:14][CH:13]=1)=[O:5])C.[OH-... | CCOC(=O)c1c(-c2ccc(C(=O)N(c3nccc4ccn(C)c34)[C@@H]3CCCN(C(=O)OC(C)(C)C)C3)cc2)cnn1C | 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 | 2 | To a solution of the compound from Step 2 (R)-tert-butyl 3-(4-(5-(ethoxycarbonyl)-1-methyl-1H-pyrazol-4-yl)-N-(1-methyl-1H-pyrrolo[2,3-c]pyridin-7-yl)benzamido)piperidine-1-carboxylate (0.2 g, 0.34 mmol) in MeOH (10 mL) was added aqueous NaOH (2 N, 1.5 mL). The reaction mixture was stirred at room temperature for 2 h. ... | Cn1ncc(-c2ccc(C(=O)N(c3nccc4ccn(C)c34)[C@@H]3CCCN(C(=O)OC(C)(C)C)C3)cc2)c1C(=O)O | null | null | null |
1,428,860 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([NH:11][C:12]2[N:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)=[CH:14][CH:13]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1>Cl.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[CH:16][N:17]=... | CC(C)(C)OC(=O)N1CCN(c2ccc(Nc3cc(Cl)cn4ccnc34)nc2)CC1 | 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 | 5 | Compound 102a (1.75 g, 4.08 mmol) was suspended in 4.0 M HCl/dioxane (10 mL) and stirred at room temperature for 5 h. It was then concentrated under reduced pressure to afford 102b (1.2 g, 81%). MS: [M+H]+ 329. | Clc1cc(Nc2ccc(N3CCNCC3)cn2)c2nccn2c1 | null | 89.5 | null |
1,320,164 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [F:1][CH2:2][CH2:3][CH2:4][OH:5].[H-].[Na+].Cl[C:9]1[N:14]=[C:13]([C:15]2[S:16][C:17]3[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:18]=3[CH:19]=2)[CH:12]=[CH:11][N:10]=1>>[F:1][CH2:2][CH2:3][CH2:4][O:5][C:9]1[N:14]=[C:13]([C:15]2[S:16][C:17]3[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:18]=3[CH:19]=2)[CH:12]=[CH:... | OCCCF | COc1ccc2cc(-c3ccnc(Cl)n3)sc2c1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2-[2-(3-Fluoropropoxy)pyrimidine-4-yl]-6-methoxybenzothiophene (1-32, 75 mg, 65%) was prepared in the same manner as in Example 31 as a pale yellow solid using 3-fluoro-1-propanol (40 mL, 0.54 mmol), sodium hydride (NaH, 22 mg, 0.54 mmol) and 2-(2-chloropyrimidine-4-yl)-6-methoxybenzothiophene (105a, 100 mg, 0.36 mmol)... | COc1ccc2cc(-c3ccnc(OCCCF)n3)sc2c1 | null | 65.4 | null |
905,864 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.Br[CH2:14][C:15]([O:17]C(C)(C)C)=[O:16].C(O)(C(F)(F)F)=O>ClCCl>[CH2:9]([O:8][C:6]([C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:14][C:15]([OH:17])=[O:16])=[CH:12][CH:11]=1)=[O:7])[CH3:10] | CCOC(=O)c1ccc(O)cc1 | CC(C)(C)OC(=O)CBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 8 | Ethyl 4-(2-tert-butyl-2-oxoethyl)benzoate obtained by carrying out reaction of ethyl 4-hydroxybenzoate with tert-butyl bromoacetate in the same manner as in Reference Example 23 (1) was dissolved in dichloromethane, mixed with TFA at room temperature and stirred overnight at room temperature. By evaporating the solvent... | CCOC(=O)c1ccc(OCC(=O)O)cc1 | null | null | null |
1,583,138 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [OH:1][C@H:2]1[CH2:11][C:10]2([CH2:14][CH2:13][CH2:12]2)[CH2:9][C:8]2[N:7]=[C:6]([CH:15]([CH3:17])[CH3:16])[C:5]([CH:18]=[O:19])=[C:4]([I:20])[C:3]1=2.[C:21]([C:25]1[CH:30]=[CH:29][C:28]([Mg]Br)=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22]>>[C:21]([C:25]1[CH:30]=[CH:29][C:28]([C@@H:18]([OH:19])[C:5]2[C:6]([CH:15]([CH3... | CC(C)(C)c1ccc([Mg]Br)cc1 | CC(C)c1nc2c(c(I)c1C=O)[C@@H](O)CC1(CCC1)C2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Obtained by starting from (S)-5′-hydroxy-4′-iodo-2′-isopropyl-6′,8′-dihydro-5′H-spiro[cyclobutane-1,7′-quinoline]-3′-carbaldehyde and 4-tert.-butylphenylmagnesium bromide. | CC(C)c1nc2c(c(I)c1[C@H](O)c1ccc(C(C)(C)C)cc1)[C@@H](O)CC1(CCC1)C2 | null | null | null |
1,315,696 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [CH2:1]([O:3][C:4](=[O:26])[C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[C:8]([NH:14][CH3:15])=[N:7][C:6]=1[N:16]1[CH2:21][CH2:20][CH:19]([C:22]([F:25])([F:24])[F:23])[CH2:18][CH2:17]1)[CH3:2]>[Pd].CCO>[CH2:1]([O:3][C:4](=[O:26])[C:5]1[CH:10]=[C:9]([NH2:11])[C:8]([NH:14][CH3:15])=[N:7][C:6]=1[N:16]1[CH2:21][CH2:20][CH:19]([C:22... | CCOC(=O)c1cc([N+](=O)[O-])c(NC)nc1N1CCC(C(F)(F)F)CC1 | 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 | null | 6 | A mixture of 6-methylamino-5-nitro-2-(4-trifluoromethyl-piperidinyl)-nicotinic acid ethylester (6.0 g, 15.9 mmol), Pd/C (800 mg) and EtOH (100 mL) is stirred under 60 psi H2-atmosphere for 6 h. The mixture is filtered, and the filtrate is concentrated. HPLC Rt=1.13 min (method A). MS m/z: 347 [M+H]+. | CCOC(=O)c1cc(N)c(NC)nc1N1CCC(C(F)(F)F)CC1 | null | null | null |
1,541,905 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]=[CH:13][N+:14]([O-])=O)=[CH:4]1)[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][CH2:13][NH2:14])=[CH:4]1)[CH3:2] | CCn1cc(C=C[N+](=O)[O-])c2ccccc21 | null | null | [Al+3] | [H-] | [Li+] | 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 | Using analogous reaction conditions and workup as described in Example 1, 1-ethyl-3-(2-nitro-vinyl)-1H-indole (4.8 g, 22.018 mmol) in dry THF (25 mL) was reacted with LAH (4.17 g, 110.091 mmol) in dry THF (25 mL). The resulting mixture was refluxed for 16 hours under nitrogen atmosphere to afford 4.1 g of the product (... | CCn1cc(CCN)c2ccccc21 | null | 98.9 | null |
154,071 | ord_dataset-128a4f3f44e844218b1c319ab4de3893 | null | 1987-01-01T00:02:00 | true | [C:1]([O:18][CH:19]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH2:20][C:21]([NH:23][C@H:24]([C:40](O)=[O:41])[CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])=[O:22])(=[O:17]... | N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)O | CCCCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCCCCCC)CC(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Starting from N-hydroxysuccinimide ester of Nα -(3-hexadecanoyloxyoctadecanoyl)-Nε -benzyloxycarbonyl-L-lysine (3 g) prepared by the method described in Example 20 (1), and Nε -benzyloxycarbonyl-L-lysine (2.24 g), Nα -[Nα -(3-hexadecanoyloxyoctadecanoyl)-Nε -benzyloxycarbonyl-L-lysyl]-Nε -benzyloxycarbonyl-L-lysine (2.... | CCCCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCCCCCC)CC(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)O | null | 67.8 | null |
1,496,323 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [OH:1][C:2]1[C:11]2[N:10]=[C:9]([NH:12][C:13](=[O:20])[C:14]3[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=3)[N:8]3[CH2:21][CH2:22][N:23]=[C:7]3[C:6]=2[CH:5]=[CH:4][C:3]=1[O:24][CH2:25][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.[H-].[Na+].Cl[CH2:37][C:38]1[CH:43]=[CH:42][C:41]([S:44]([CH3:47])(=[O:46])=[O:45... | CS(=O)(=O)c1ccc(CCl)cc1 | O=C(NC1=Nc2c(ccc(OCCCN3CCOCC3)c2O)C2=NCCN12)c1cccnc1 | 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 | 16 | N-[7-Hydroxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]nicotinamide (Intermediate H, 0.09 g, 0.20 mmol) was suspended in DMF (2.0 mL) and NaH (0.02 g, 0.30 mmol, 60%) were added. After 20 min at rt 1-(chloromethyl)-4-(methylsulfonyl)benzene (0.06 g, 0.30 mmol) was added and the mixture was st... | CS(=O)(=O)c1ccc(COc2c(OCCCN3CCOCC3)ccc3c2N=C(NC(=O)c2cccnc2)N2CCN=C32)cc1 | null | 70.3 | null |
1,287,928 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [C:1]1(=[O:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[Si:18]([CH3:21])([CH3:20])[CH3:19]>CN(C=O)C>[C:1]1([O:9][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1 | O=C1CCCCCCC1 | C[Si](C)(C)Cl | null | null | 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 | null | 15 | To a solution of cyclooctanone (40.0 g, 316 mmol) in 200 mL of anhydrous DMF were added triethylamine (TEA, 93.0 mL, 666 mmol) and chlorotrimethylsilane (84.0 mL, 666 mmol). The reaction was heated to reflux. After 15 h, the reaction was quenched with 20 mL of H2O and the DMF was removed on a rotary evaporator. The res... | C[Si](C)(C)OC1=CCCCCCC1 | null | 92.7 | null |
1,545,597 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [O:1]=[C:2]1[N:7]([C:8]2[S:9][CH:10]=[CH:11][N:12]=2)[CH:6]=[C:5]([C:13]([O:15]C)=[O:14])[CH:4]=[CH:3]1.[OH-].[Li+].[CH3:19]O>O>[CH3:19][C:6]1[N:7]([C:8]2[S:9][CH:10]=[CH:11][N:12]=2)[C:2](=[O:1])[CH:3]=[CH:4][C:5]=1[C:13]([OH:15])=[O:14] | CO | COC(=O)c1ccc(=O)n(-c2nccs2)c1 | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 75 | 5 | After 680 mg (2.88 mmol) of methyl 6-oxo-1-(2-thiazolyl)-1,6-dihydro-3-pyridinecarboxylate was dissolved in 12 mL of methanol and 4 mL of water, 207 mg (8.64 mmol) of lithium hydroxide was added to the solution. Afterward, the resulting reaction solution was stirred at about 75° C. for 5 hours. After termination of the... | Cc1c(C(=O)O)ccc(=O)n1-c1nccs1 | null | 73 | null |
1,283,906 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].[CH:9]1([NH:15][C:16]2[C:21]([CH:22]=O)=[CH:20][N:19]=[C:18]3[N:24]([CH2:27][CH3:28])[N:25]=[CH:26][C:17]=23)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>C(O)C>[CH:9]1([NH:15][C:16]2[C:21]([CH:22]=[N:2][OH:3])=[CH:20][N:19]=[C:18]3[N:24]([CH2:27][CH3:28])[N:25]=[CH:26][C:17]=23)[CH2:14]... | CCn1ncc2c(NC3CCCCC3)c(C=O)cnc21 | NO | null | CC(=O)[O-] | Cl | [Na+] | 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 | 2 | Hydroxylamine hydrochloride (0.255 gm, 0.0036 mole) and sodium acetate (0.301 gm, 0.0036 mole) were added to a stirred solution of 4-(cyclohexylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde (0.250 gm, 0.0009 mole) (example 7) in ethanol. The reaction mixture was allowed to stir at room temperature for about ... | CCn1ncc2c(NC3CCCCC3)c(C=NO)cnc21 | null | null | null |
585,696 | ord_dataset-cb5dd7a8b94e4f19a9148a1904b0dcb6 | null | 2003-01-01T00:03:00 | true | [CH3:1][C:2](=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3](O)=[O:4].S(Cl)([Cl:15])=O>CN(C=O)C>[CH3:1][C:2](=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([Cl:15])=[O:4] | CC(=Cc1ccccc1)C(=O)O | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 0.08 | α-methylcinnamic acid (45 g) and thionyl chloride (50 g) was stirred at 20-30° C. After 5 min, 0.3 ml of DMF was added and kept stirring at 20-30° C. for 1 hour to give crude of α-methylcinnamoyl chloride (solution A) | CC(=Cc1ccccc1)C(=O)Cl | null | null | null |
1,683,491 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [OH:1][CH:2]1[O:6][C@H:5]2[CH2:7][C:8]([CH:10]=[O:11])=[CH:9][C@H:4]2[CH2:3]1.[CH:12]1(O)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.[O-]S([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[CH:12]1([O:1][CH:2]2[O:6][C@H:5]3[CH2:7][C:8]([CH:10]=[O:11])=[CH:9][C@H:4]3[CH2:3]2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1 | O=CC1=C[C@H]2CC(O)O[C@H]2C1 | OC1CCCCC1 | null | O=S(=O)([O-])[O-] | [Mg+2] | 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 | null | Partially purified residue containing lactol 7 from a procedure in accordance with Example 3E (6.24 g, 12.5% detected by NMR, 40.5 mmol, 1 eq.) was dissolved in CH2Cl2 (90 ml) and stirred at room temperature. Cyclohexanol (14.2 g, 14.9 ml, 3.5 eq.) was added via syringe and Amberlyst 15 (825 mg) and MgSO4 (16.83 g) wer... | O=CC1=C[C@H]2CC(OC3CCCCC3)O[C@H]2C1 | null | null | null |
1,084,300 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | I[C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]3[C:16]([C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:15][N:14]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:11]3=[N:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.Cl.[NH:32]1[CH2:35][CH:34]([OH:36])[CH2:33]1>>[OH:36][CH:34]1[CH2:35][N:32]([C:2]2[CH:3]=[C:4]([C... | OC1CNC1 | CC(C)(C)C(=O)c1cn(COCC[Si](C)(C)C)c2ncc(-c3cccc(I)c3)nc12 | 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 | 1-[2-[3-(3-Hydroxy-azetidin-1-yl)-phenyl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one was prepared starting from 1-[2-(3-iodo-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one and azetidin-3-ol hydrogen chloride followin... | CC(C)(C)C(=O)c1cn(COCC[Si](C)(C)C)c2ncc(-c3cccc(N4CC(O)C4)c3)nc12 | null | null | null |
966,138 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [CH2:1]([C:3]1(O)[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2].[CH3:14][O:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:24]=1[NH:23][CH:22]=[CH:21]2>>[CH2:1]([C:3]1([C:21]2[C:20]3[C:24](=[C:16]([O:15][CH3:14])[CH:17]=[CH:18][CH:19]=3)[NH:23][CH:22]=2)[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:... | CCC1(O)CCc2cc(F)ccc21 | COc1cccc2cc[nH]c12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Utilizing 1-ethyl-5-fluoro-indan-1-ol and 7-methoxyindole, the title compound is prepared as in example 1. 123 mg (59%). LC-MS m/z 310.2 (M++1). | CCC1(c2c[nH]c3c(OC)cccc23)CCc2cc(F)ccc21 | null | null | null |
459,528 | ord_dataset-aa5bc55d09b7465ab353e144a7ac3ad1 | null | 2000-01-01T00:03:00 | true | [F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]1([CH2:13][N:14]2[CH:18]=[N:17][CH:16]=[N:15]2)[C@H:11]([CH3:12])[O:10]1.[CH3:19][C:20]1[S:21][CH:22]=[C:23]([C:25]2[CH:30]=[CH:29][C:28]([N:31]3[CH:35]=[CH:34][NH:33][C:32]3=[O:36])=[CH:27][CH:26]=2)[N:24]=1>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@... | C[C@@H]1O[C@@]1(Cn1cncn1)c1ccc(F)cc1F | Cc1nc(-c2ccc(-n3cc[nH]c3=O)cc2)cs1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | (2R,3S)-2-(2,4-Difluorophenyl)-3-methyl-2-(1H-1,2,4-triazol-1-yl)methyloxirane was reacted with 1-[4-(2-methyl-4-thiazolyl)phenyl]-2(1H,3H)-imidazolone in the same manner as in Working Example 11 to give 1-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(2-methyl-4-thiazolyl)phe... | Cc1nc(-c2ccc(-n3ccn([C@H](C)[C@](O)(Cn4cncn4)c4ccc(F)cc4F)c3=O)cc2)cs1 | null | null | null |
555,904 | ord_dataset-f483e698250b4da0a84f425c7bfa965a | null | 2002-01-01T00:08:00 | true | Cl.[N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12](Cl)=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[C:15]12([NH2:25])[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH2:16]1)[CH2:22]2.N1C=CC=CC=1>O>[C:15]12([NH:25][C:12]([C:8]3[CH:7]=[C:6]4[C:11](=[CH:10][CH:9]=3)[N:2]=[CH:3][CH:4]=[CH:5]4)=[O:13])[CH2:22][CH:21]3[... | NC12CC3CC(CC(C3)C1)C2 | O=C(Cl)c1ccc2ncccc2c1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | Prepared from 6-quinolinecarbonyl chloride hydrochloride (1.51 g, 10 mmol), 1-adamantanamine (1.73 g, 10 mmol), pyridine (5 mL), and water (200 mL) yielding 330 mg (11%) of (42): | O=C(NC12CC3CC(CC(C3)C1)C2)c1ccc2ncccc2c1 | null | 10.8 | null |
296,223 | ord_dataset-ec7cb3d5a8704f64b01d401ea555974f | null | 1994-01-01T00:09:00 | true | [CH3:1][C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.[CH2:8]=[O:9]>>[OH:9][CH2:8][CH2:1][C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1 | Cc1cnccn1 | C=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 | A mixture of 90.0 g (956 mmol) of 2-methylpyrazine and 6.4 g (212 mmol) of paraformaldehyde was heated in a stainless steel autoclave at 165° C. for 5 hours, The residue was distilled under iced aspirator pressure (ca. 10 mmHg) to yield 8.28 g (32%) of a light pink oil. | OCCc1cnccn1 | null | 31.5 | null |
1,474,852 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | N[C:2]1[CH:17]=[C:16]([Br:18])[CH:15]=[CH:14][C:3]=1[C:4]([NH:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].C(O)C.N([O-])=O.[Na+]>Cl.O>[Br:18][C:16]1[CH:15]=[C:14]2[C:3]([C:4](=[O:5])[NH:6][N:7]2[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:2][CH:17]=1 | Nc1cc(Br)ccc1C(=O)NNc1ccccc1 | null | null | Cl | O=N[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | 76 | null | Into a 100-mL 3-necked round-bottom flask, was placed a solution of 2-amino-4-bromo-N′-phenylbenzohydrazide (4 g, 13.07 mmol, 1.00 equiv) in 1N HCl:Ethanol=1:1 (40 mL). The resulting solution was heated to 76° C. The solid dissolved to yield red solution. To the resulting mixture was then added a solution of NaNO2 (2.7... | O=c1[nH]n(-c2ccccc2)c2cc(Br)ccc12 | null | null | null |
1,342,827 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [CH3:1][O:2][C:3]1[N:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:11](=O)[NH:10][C:9]([CH2:14][CH2:15][CH2:16][N:17]1[C:25](=[O:26])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]1=[O:27])=[CH:8]2.O=P(Cl)(Cl)[Cl:30]>CC#N>[Cl:30][C:11]1[C:12]2[C:7](=[CH:6][CH:5]=[N:4][C:3]=2[O:2][CH3:1])[CH:8]=[C:9]([CH2:14][CH2:15][CH2:16][N... | O=P(Cl)(Cl)Cl | COc1nccc2cc(CCCN3C(=O)c4ccccc4C3=O)[nH]c(=O)c12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | null | 2-(3-(8-Methoxy-1-oxo-1,2-dihydro-2,7-naphthyridin-3-yl)propyl)isoindoline-1,3-dione (200 mg, 0.55 mmol) is dissolved in CH3CN (2 mL) and POCl3 (59 uL, 0.64 mmol) The mixture is stirred at 80° C. for 3 hours. POCl3 is removed and neutralized with sat. NaHCO3. The compound is extracted with CHCl3 and the organic layer i... | COc1nccc2cc(CCCN3C(=O)c4ccccc4C3=O)nc(Cl)c12 | null | null | null |
1,682,696 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[CH3:23][C:24]1([CH3:27])[CH2:26][O:25]1.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21]... | CC1(C)CO1 | Cn1cc(Br)cc(Nc2ccc(N3CCNCC3)cn2)c1=O | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 110 | null | A sealed tube equipped with a magnetic stirrer was charged with 5-bromo-1-methyl-3-(5-(piperazin-1-yl)pyridin-2-ylamino)pyridin-2(1H)-one 101j (500 mg, 1.37 mmol), 2,2-dimethyloxirane (990 mg, 13.7 mmol), Cs2CO3 (1.3 g, 4.11 mmol), and CH3CN (15 mL). After three cycles of vacuum/argon flush, the mixture was heated at 1... | Cn1cc(Br)cc(Nc2ccc(N3CCN(CC(C)(C)O)CC3)cn2)c1=O | null | null | null |
381,053 | ord_dataset-993feac5ecf54388aa6326a220e46db3 | null | 1997-01-01T00:10:00 | true | [CH:1]1[C:14]2[C:13]3([CH2:16][N:17]4[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]4)[CH2:15][CH:6]([C:7]4[C:12]3=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1>>[CH:11]1[C:12]2[C:13]3([CH2:16][N:17]4[CH2:22][CH2:21][C:20]([C:25]5[CH:30]=[CH:2... | COc1ccc(Br)cc1 | O=C1CCN(CC23CC(c4ccccc42)c2ccccc23)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using a procedure similar to that described in example except starting with 1-(9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)-4-piperidinone (described in example 5d) and employing 4-bromoanisole, the hydrochloride salt of the title compound was formed in 72% yield as a white solid, mp 228°-231° C. elemental Analysis f... | COc1ccc(C2(O)CCN(CC34CC(c5ccccc53)c3ccccc34)CC2)cc1 | null | 72 | null |
646,044 | ord_dataset-c975a50a7600448fabd558f4a94a3e29 | null | 2004-01-01T00:08:00 | true | [Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:13])=[C:9]([OH:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]#[N:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.O[CH2:48][CH2:49][N:50]1[CH2:55][CH2:54][O:53][CH2:52][CH2:51]1>>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:13])=[C:9]([O:12][CH2:48][CH2:49][N:50]3[CH2:55][C... | N#Cc1cnc2cc(F)c(O)cc2c1Cl | OCCN1CCOCC1 | 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 | null | null | null | null | null | null | null | null | null | null | null | null | null | Following the procedure used to prepare Reference Example 14, reaction of 4-chloro-7-fluoro-6-hydroxy-3-quinolinecarbonitrile with triphenyl phosphine, diethyl azodicarboxylate and 4-(2-hydroxyethyl)morpholine provides 4-chloro-7-fluoro-6-(2-morpholin-4-ylethoxy)-3-quinolinecarbonitrile in 57% yield. An analytical samp... | N#Cc1cnc2cc(F)c(OCCN3CCOCC3)cc2c1Cl | null | 57 | null |
1,459,761 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [NH2:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[N:14]([O:16][O-])=[O:15]>P([O-])([O-])([O-])=O>[N+:14]([NH:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)([O-:16])=[O:15] | N[C@@H](Cc1ccc(O)cc1)C(=O)O | O=NO[O-] | null | O=P([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 | null | null | Nitration of L-tyrosine: Peroxynitrite (0.44 μmol) was reacted with 0.16 μmol of L-tyrosine in 2 mL phosphate buffer solution, pH 7.4 at T=24° C. for 5 min. The concentration of such formed nitrotyrosine was estimated by recording the 438 nm absorbance (ε=4200 M−1cm−1) of basified solutions (via the addition of 0.2 ml ... | O=C(O)[C@H](Cc1ccc(O)cc1)N[N+](=O)[O-] | null | null | null |
1,514,136 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [OH:1][CH2:2][C@@H:3]([CH2:19][CH2:20][CH2:21][CH3:22])[C:4](N1[C@@H](CC2C=CC=CC=2)COC1=O)=[O:5].[OH:23]O.O.[OH-].[Li+]>C1COCC1.O.O>[OH:1][CH2:2][C@@H:3]([CH2:19][CH2:20][CH2:21][CH3:22])[C:4]([OH:5])=[O:23] | CCCC[C@H](CO)C(=O)N1C(=O)OC[C@@H]1Cc1ccccc1 | OO | 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 | 0 | 8 | To a 2000 mL roundbottom flask was added (4S)-3-[(2R)-2-(hydroxymethyl)hexanoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one (4) (82 g, 0.268 mol) in THF/water (4:1, 750 mL). The solution was cooled to 0° C. and H2O2 (130 mL, 1.07 mol) was added dropwise, followed by lithium hydroxide monohydrate (22.58 g, 0.537 mol) in wate... | CCCC[C@H](CO)C(=O)O | null | 107.2 | null |
168,828 | ord_dataset-37d3220f708c49ad839bab296b722248 | null | 1988-01-01T00:03:00 | true | [N+:1]1([O-:10])[CH:6]=[CH:5][C:4]([C:7]([OH:9])=O)=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:23][C:24]1[CH:25]=[C:26]([NH2:32])[C:27]([NH2:31])=[CH:28][C:29]=1[Cl:30]>CN(C)C=O.ClCCl>[NH2:32][C:26]1[CH:25]=[C:24]([Cl:23])[C:29]([Cl:30])=[CH:28][C:27]=1[NH:31][C:7]([C:4]1[CH:3]=[CH:2][N+:1]([O-:10])=[CH:6][CH:5]=1)=[... | Nc1cc(Cl)c(Cl)cc1N | O=C(O)c1cc[n+]([O-])cc1 | null | O=C(n1ccnc1)n1ccnc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | ClCCl | null | null | null | null | null | null | null | null | null | null | 4 | A suspension of 4-pyridinecarboxylic acid-1-oxide (2.84 g, 20.4 mmol) and 1,1'-carbonyldiimidazole (3.64 g, 22.4 mmol) in dry dimethylformamide (50 ml) was stirred for 4 hours under an air-lock and the resulting solution added dropwise over 1 hour to a stirred solution of 4,5-dichloro-1,2-benzenediamine (7.23 g, 40.8 m... | Nc1cc(Cl)c(Cl)cc1NC(=O)c1cc[n+]([O-])cc1 | null | 16.4 | null |
298,325 | ord_dataset-b6309a86b70f4ca08fd301828cacf950 | null | 1994-01-01T00:10:00 | true | [C:1]([C:5]1[CH:6]=[C:7]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:8]2[O:12][C:11](=[O:13])[CH:10]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]([O:24][CH2:25]C)=[O:23])=[CH:16][CH:15]=3)[C:9]=2[CH:27]=1)([CH3:4])([CH3:3])[CH3:2]>CO>[C:1]([C:5]1[CH:6]=[C:7]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:8]2[O:12][C:11](=[O:13])... | CCOC(=O)COc1ccc(C2C(=O)Oc3c2cc(C(C)(C)C)cc3C(C)(C)C)cc1 | 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 | A mixture of 5.0 g (11.8 mmol) of 5,7-di-tert-butyl-3-(4-ethoxycarbonylmethoxyphenyl)benzofuran-2-one (Compound (113), Example 6) and 2 g of strong acidic ion exchanger (Dowex) in 50 ml of methanol is refluxed for 4 hours. The reaction mixture is filtered, and the filtrate is concentrated on a vacuum rotary evaporator.... | COC(=O)COc1ccc(C2C(=O)Oc3c2cc(C(C)(C)C)cc3C(C)(C)C)cc1 | null | 61.9 | null |
690,461 | ord_dataset-6214af00a7eb47f3887ef21a94320a7e | null | 2005-01-01T00:11:00 | true | [C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:9][C:10]1[C:18]2[C:13](=[N:14][C:15]([CH3:21])=[CH:16][C:17]=2[CH:19]=[O:20])[S:12][C:11]=1[C:22]([NH2:24])=[O:23].[NH4+].[Cl-]>C1COCC1>[NH2:9][C:10]1[C:18]2[C:13](=[N:14][C:15]([CH3:21])=[CH:16][C:17]=2[CH:19]([OH:20])[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[S:12]... | Br[Mg]c1ccccc1 | Cc1cc(C=O)c2c(N)c(C(N)=O)sc2n1 | null | [Cl-] | [NH4+] | 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 | 1.5 | To a suspension of 314 mg CeCl3 in 3 mL dry THF at −78° C. was added 0.425 mL 3M phenylmagnesium bromide and the reaction was stirred 1.5 h under Ar. Then, 50 mg of 3-amino-4-formyl-6-methyl-thieno[2,3-b]pyridine-2-carboxylic acid amide was added and the reaction was stirred 5 h in the cold and then allowed to warm to ... | Cc1cc(C(O)c2ccccc2)c2c(N)c(C(N)=O)sc2n1 | null | null | null |
1,463,638 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([O:9][CH2:10][C:11]2[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=2[F:18])[C:5]([NH2:8])=[N:6][CH:7]=1.Cl[CH:20]([C:26]([CH3:28])=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([O:9][CH2:10][C:11]2[C:12]([F:18])=[CH:13][CH:14]=[CH:15][C:16]=2[F:17])[C:5]2[N:6]([C:20]([C:21... | Nc1ncc(Cl)cc1OCc1c(F)cccc1F | CCOC(=O)C(Cl)C(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | 40 g of 5-chloro-3-[(2,6-difluorobenzyl)oxy]pyridine-2-amine (Example 14A; 147.8 mmol; 1 equivalent) were initially charged in 800 ml of ethanol, 30 g of powdered molecular sieve 3A and 128 g of ethyl 2-chloroacetoacetate (739 mmol, 5 equivalents) were added and the mixture was heated at reflux overnight. The reaction ... | CCOC(=O)c1c(C)nc2c(OCc3c(F)cccc3F)cc(Cl)cn12 | null | null | null |
882,361 | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | null | 2009-01-01T00:05:00 | true | [N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][N:11]2[C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])=[CH:6][CH:5]=1)([O-:3])=[O:2].II.[I:22]([O-])(=O)=O.[K+].O>S(=O)(=O)(O)O>[I:22][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][CH2:10][N:11]2[C:14](=[O:19])[C:15]([F:18])([F:16])[F:17... | O=C(N1CCCc2ccc([N+](=O)[O-])cc21)C(F)(F)F | [O-][I+2]([O-])[O-] | null | II | O=S(=O)(O)O | [K+] | 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 | 0 | 3 | A solution of 7-nitro-1-trifluoroacteyl-1,2,3,4-tetrahydroquinoline (D4) (2 g, 7.3 mmol) in conc. sulfuric acid (10 ml) was cooled to 0° C. and treated with iodine (1.11 μg, 4.4 mmol) and potassium iodate (0.625 g, 2.9 mmol). The reaction was stirred at 0° C. for 3 h then room temperature for 2 h. The reaction mixture ... | O=C(N1CCCc2c(I)cc([N+](=O)[O-])cc21)C(F)(F)F | null | 36.2 | null |
853,690 | ord_dataset-faa0236be76c4501841c954527cd1b6c | null | 2008-01-01T00:12:00 | true | [CH2:1]([NH:6][C:7]1[N:8]=[CH:9][NH:10][C:11]=1[C:12](=[S:14])[NH2:13])[CH2:2][CH2:3][CH2:4][CH3:5].[CH3:15]I>CC(C)=O>[CH2:1]([NH:6][C:7]1[N:8]=[CH:9][NH:10][C:11]=1[C:12]([S:14][CH3:15])=[NH:13])[CH2:2][CH2:3][CH2:4][CH3:5] | CCCCCNc1nc[nH]c1C(N)=S | CI | null | null | null | 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 | 8 | To a solution of 4-(pentylamino)-1H-imidazole-5-carbothioamide (1.0 g, 4.7 mmol) in acetone (40 mL) was added methyl iodide (0.80 g, 5.6 mmol) dropwise. The mixture was stirred at room temperature overnight. The solvent was removed and the residue was diluted with water and ethyl acetate. The organic layer was washed w... | CCCCCNc1nc[nH]c1C(=N)SC | null | 112.8 | null |
1,749,992 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | C([O:3][C:4](=[O:31])[CH2:5][CH2:6][NH:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:30])[C:14]=2[C:18](=[O:29])[NH:19][CH2:20][CH:21]2[CH2:26][CH2:25][C:24]([F:28])([F:27])[CH2:23][CH2:22]2)[N:9]=1)C.O.[OH-].[Li+]>C1COCC1.O>[Cl:30][C:13]1[C:14]([C:18](=[O:29])[NH:19][CH2:20][CH:21]2[CH2:26][CH2:25][C... | CCOC(=O)CCNc1ccc2c(C(=O)NCC3CCC(F)(F)CC3)c(Cl)ccc2n1 | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of 3-{6-Chloro-5-[(4,4-difluoro-cyclohexylmethyl)-carbamoyl]-quinolin-2-ylamino}-propionic acid ethyl ester (80 mg, 0.17 mmol, 1.00 eq) in THF (8.00 mL, 100 V) and Water (2.00 mL, 25 V) was added Lithium Hydroxide Monohydrate (14.72 mg, 0.35 mmol, 2.00 eq). The reaction mixture was stirred for overnight a... | O=C(O)CCNc1ccc2c(C(=O)NCC3CCC(F)(F)CC3)c(Cl)ccc2n1 | null | 47.1 | null |
1,019,590 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | [CH3:1][N:2]([CH3:27])[C:3]([C:5]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:8]2([CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)[CH2:7][CH:6]=1)=[O:4].C(O)(C(F)(F)F)=O>ClCCl>[CH3:1][N:2]([CH3:27])[C:3]([C:5]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:8]2([CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH... | CN(C)C(=O)C1=CCC2(CCN(C(=O)OC(C)(C)C)CC2)c2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | A solution of the dimethylamide (B2) (156 mg) in dichloromethane (5 ml) was treated with TFA (1 ml) for 1 h. After concentration and co-evaporation with acetonitrile, the residue was dissolved in dichloromethane, washed with a mixture of brine and 1 ml 6N NaOH, dried (Na2SO4), and concentrated to give N,N-dimethyl-2H-s... | CN(C)C(=O)C1=CCC2(CCNCC2)c2ccccc21 | null | 118.6 | null |
556,098 | ord_dataset-f483e698250b4da0a84f425c7bfa965a | null | 2002-01-01T00:08:00 | true | Cl[C:2]1[C:11]([C:12]#[N:13])=[C:10]2[C:5]([C:6](=[O:20])[C:7]([C:17]([OH:19])=[O:18])=[CH:8][N:9]2[CH:14]2[CH2:16][CH2:15]2)=[CH:4][C:3]=1[F:21].[C@H:22]12[CH2:30][NH:29][CH2:28][C@@H:27]1[NH:26][CH2:25][CH2:24][O:23]2.C(N(CC)CC)C>C(#N)C>[C:12]([C:11]1[C:2]([C@:22]23[CH2:30][NH:29][CH2:28][C@@H:27]2[NH:26][CH2:25][CH2... | N#Cc1c(Cl)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12 | C1CO[C@H]2CNC[C@@H]2N1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CC#N | null | null | null | null | null | null | null | null | null | null | null | 1.00 g (3.26 mmol) of 7-chloro-8-cyano-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylicacid are stirred under argon at 40-45° C. for 25 hours with 501 mg (3.91 mmol) of (1S,6S)-2-oxa-5,8-diazabicyclo[4.3.0]nonane and 0.9 ml of triethylamine in 30 ml of acetonitrile. All volatile components are removed in ... | N#Cc1c([C@]23CNC[C@@H]2NCCO3)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12 | null | null | null |
1,731,904 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [OH:1][C@H:2]1[CH2:6][N:5]([CH3:7])[C@H:4]([C:8]([O:10][CH3:11])=[O:9])[CH2:3]1.N1C=CN=C1.[C:17]([Si:21]([CH3:24])([CH3:23])Cl)([CH3:20])([CH3:19])[CH3:18]>ClCCl>[Si:21]([O:1][C@H:2]1[CH2:6][N:5]([CH3:7])[C@H:4]([C:8]([O:10][CH3:11])=[O:9])[CH2:3]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:24])[CH3:23] | CC(C)(C)[Si](C)(C)Cl | COC(=O)[C@@H]1C[C@@H](O)CN1C | null | c1c[nH]cn1 | 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 | 12 | Methyl (2S,4R)-4-hydroxy-1-methyl-pyrrolidine-2-carboxylate 3b (6 g, 37 mmol) was dissolved in 100 mL of dichloromethane, followed by addition of imidazole (7.70 g, 113 mmol) and tert-butyl dimethylchlorosilane (6.80 g, 45 mmol) successively. After stirring for 12 hours, the reaction mixture was diluted with 100 mL of ... | COC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C(C)(C)C)CN1C | null | null | null |
1,345,082 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27](=[O:28])[C:26]4[C:21](=[CH:22][C:23](Br)=[CH:24][CH:25]=4)[O:20][C:19]=3[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[NH:37]1[C:41](B(O)O)=[CH:40][CH:39]=[N:38]1.C(=O)(... | OB(O)c1ccn[nH]1 | CC(C)(C)OC(=O)NC1(c2ccc(-c3c(-c4ccccc4)oc4cc(Br)ccc4c3=O)cc2)CCC1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | COCCOC | null | null | null | null | null | null | null | null | null | 150 | null | {1-[4-(7-Bromo-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (81 mg, 0.15 mmol), 1H-pyrazole-5-boronic acid (22 mg, 0.2 mmol), tetrakis(triphenylphosphine)palladium (0) (17 mg, 0.015 mmol) and sodium carbonate (32 mg, 0.30 mmol) were suspended in DME (2 mL) and water (1 mL) in a mic... | CC(C)(C)OC(=O)NC1(c2ccc(-c3c(-c4ccccc4)oc4cc(-c5ccn[nH]5)ccc4c3=O)cc2)CCC1 | null | 45 | null |
705,617 | ord_dataset-c408dfed796e4354b61e312e67f7143f | null | 2006-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][CH2:11][NH:12][CH2:13][CH:14]([C:18]2[CH:23]=[CH:22][C:21]([I:24])=[CH:20][CH:19]=2)[CH2:15][CH:16]=[CH2:17])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C1N=CN([C:30](N2C=NC=C2)=[O:31])C=1>C1(C)C=CC=CC=1.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:10][CH2:11][N:12]([CH2:13][CH:14]([C:18]3[CH:... | O=C(n1ccnc1)n1ccnc1 | C=CCC(CNCCNc1cc(Cl)cc(Cl)c1)c1ccc(I)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 100 | null | To a stirred solution of N-(3,5-dichloro-phenyl)-N′-[2-(4-iodo-phenyl)-pent-4-enyl]-ethane-1,2-diamine (0.386 g, 0.81 mmol) in toluene (10 mL) was added CDI (0.18 g, 1.1 mmol, 1.4 eq). The mixture was heated to 100° C. for 16 h, then cooled to room temperature, diluted with EtOAc (25 mL) and washed twice with saturated... | C=CCC(CN1CCN(c2cc(Cl)cc(Cl)c2)C1=O)c1ccc(I)cc1 | null | 31.5 | null |
852,773 | ord_dataset-faa0236be76c4501841c954527cd1b6c | null | 2008-01-01T00:12:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=O)[C:10](=[CH:13]N(C)C)[CH2:9][C:8](=[O:17])[NH:7][C:6]=2[CH:18]=1.[N+]([O-])(O)=O.[I:23][C:24]1[CH:25]=[C:26]([NH:30][C:31]([NH2:33])=[NH:32])[CH:27]=[CH:28][CH:29]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[N:32]=[C:31]([NH:30][C:26]4[CH:27]=[CH:28][CH:29]=[C:24]([I:23])[CH:25]=4... | CN(C)C=C1CC(=O)Nc2cc(Cl)ccc2C1=O | N=C(N)Nc1cccc(I)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=[N+]([O-])O | null | null | null | null | null | null | null | null | null | null | null | null | In a manner similar to that described for method I, 8-chloro-4-dimethylaminomethylene-3,4-dihydro-1H-benzo[b]azepine-2,5-dione (v-j) and N-(3-iodo-phenyl)-guanidine nitrate were converted to I-58 (50%): HRMS Calcd. for C18H12ClIN4O: 462.9822, Found 462.9838. | O=C1Cc2cnc(Nc3cccc(I)c3)nc2-c2ccc(Cl)cc2N1 | null | null | null |
260,915 | ord_dataset-ab5ba9f863cb41d9924be0bb3c730818 | null | 1993-01-01T00:01:00 | true | [OH:1][CH:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]#[N:12])[C:5]=2[CH2:4][CH2:3]1.[C:13](OC(=O)C)(=[O:15])[CH3:14].O.[Cl-].[Na+]>N1C=CC=CC=1>[C:13]([O:1][CH:2]1[C:10]2[C:5](=[C:6]([C:11]#[N:12])[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1)(=[O:15])[CH3:14] | CC(=O)OC(C)=O | N#Cc1cccc2c1CCC2O | null | [Cl-] | [Na+] | 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 | 20 | 16 | 3.89 g of (RS) 1-hydroxy-4-indanecarbonitrile in 39 ml of pyridine is cooled to 0° C., 3.45 ml of acetic anhydride is added drop by drop, and the whole is agitated for 16 hours at 20° C. The reaction mixture is poured into 300 ml of water containing sodium chloride and extracted with isopropyl ether; the ethereal phase... | CC(=O)OC1CCc2c(C#N)cccc21 | null | null | null |
1,331,064 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [N:1]([CH2:4][CH2:5][CH2:6][N:7]1[CH:15]=[N:14][C:13]2[C:8]1=[N:9][CH:10]=[N:11][C:12]=2[NH2:16])=[N+]=[N-].[H][H]>[Pd].CO>[NH2:1][CH2:4][CH2:5][CH2:6][N:7]1[CH:15]=[N:14][C:13]2[C:8]1=[N:9][CH:10]=[N:11][C:12]=2[NH2:16] | [H][H] | [N-]=[N+]=NCCCn1cnc2c(N)ncnc21 | 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 | null | A mixture of 9-(3-azidopropyl)adenine and 5% palladium on carbon in methanol was reacted with hydrogen gas at room temperature for 22 hours. The catalyst was removed by filtration, the solvent was removed to give 9-(3-aminopropyl)adenine as a white solid. The reference for the synthetic procedure is Zhang et al., “Synt... | NCCCn1cnc2c(N)ncnc21 | null | null | null |
1,704,721 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@@H:26]3[CH2:31][CH2:30][CH2:29][CH2:28][NH:27]3)=[N:9][C:10]=2[C:11]2[CH:25]=[CH:24][C:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[O:16])=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1.[CH3:32][O:33][CH2:34]/[CH:35]=[CH:36]/[C:37](O)=[O:38]>>[NH2:1][C:2]1[C:3]2[N:4]([C:8](... | Nc1nccn2c([C@@H]3CCCCN3)nc(-c3ccc(C(=O)Nc4ccccn4)cc3)c12 | COC/C=C/C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This compound was prepared, in an analogous manner as described in Example 2, from (S)-4-(8-amino-3-(piperidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide (intermediate 21) and (E)-4-methoxybut-2-enoic acid (intermediate 3), to afford the title compound (21.1 mg, 54.3%). Data: LCMS (B) Rt: 2.22 min; m/z ... | COC/C=C/C(=O)N1CCCC[C@H]1c1nc(-c2ccc(C(=O)Nc3ccccn3)cc2)c2c(N)nccn12 | null | 54.3 | null |
950,939 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | [CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:31])=[C:8]2[C:15]([C:16]#[N:17])=[C:14]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[N:13]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:9]2=[C:10](Br)[N:11]=1)=[O:5])[CH3:2].[C:32]([Cu])#[N:33]>>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:31])=[C:8]2[C:15]([C:16]#[N:17])=[C:14](... | N#C[Cu] | CCOC(=O)c1nc(Br)c2c(c1O)c(C#N)c(-c1ccc(F)cc1)n2-c1ccccc1 | null | null | null | null | null | null | null | 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 in analogy to that of Example 105(a) from 7-bromo-3-cyano-2-(4-fluoro-phenyl)-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester and CuCN. The title compound, ESI MS (m/z): 427 (M+H)+. | CCOC(=O)c1nc(C#N)c2c(c1O)c(C#N)c(-c1ccc(F)cc1)n2-c1ccccc1 | null | null | null |
281,988 | ord_dataset-1953a9402dda47b6bcfe3e3cb9ab8a07 | null | 1993-01-01T00:12:00 | true | [CH3:1][N:2]1[CH:6]=[C:5]([N+:7]([O-:9])=[O:8])[N:4]=[C:3]1[C:10]([OH:12])=O.C(Cl)(=O)C([Cl:16])=O>C1COCC1>[CH3:1][N:2]1[CH:6]=[C:5]([N+:7]([O-:9])=[O:8])[N:4]=[C:3]1[C:10]([Cl:16])=[O:12] | O=C(Cl)C(=O)Cl | Cn1cc([N+](=O)[O-])nc1C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of 1-methyl-4-nitroimidazole-2-carboxylic acid (2.0 g, 0.012 mol) in dry THF (20 mL) was slowly added oxalyl chloride (6 mL). The solution was heated to reflux for 45 minutes, and the solvent and excess oxalyl chloride were removed under reduced pressure to give 1-methyl-4-nitroimidazole-2-carbonyl chlori... | Cn1cc([N+](=O)[O-])nc1C(=O)Cl | null | null | null |
456,202 | ord_dataset-4a5b4fffffb34daa876fff1f127a4135 | null | 2000-01-01T00:01:00 | true | [Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:12]([C:26]3[C:34]([Cl:35])=[CH:33][C:29]4[O:30][CH2:31][O:32][C:28]=4[CH:27]=3)[C:13](NS(C3C=CC(C)=CC=3)(=O)=O)=[O:14])=[CH:7][N:8]2C)=[CH:4][CH:3]=1.[CH2:36]([O:38]CC)C>CCCCCC>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:12]([C:26]3[C:34]([Cl:35])=[CH:33][C:29]4[O:30][CH2:31][O:3... | CCOCC | Cc1ccc(S(=O)(=O)NC(=O)C(c2cc3c(cc2Cl)OCO3)c2cn(C)c3cc(Br)ccc23)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCC | null | null | null | null | null | null | null | null | null | null | null | null | The subtitle compound was prepared following the procedure of Example 92(c), using methyl 2-bromo-2-(6-chloro-1,3-benzodioxol-5-yl)acetate from step (b), m.p. 172-174° C. from diethyl ether and hexane. | COC(=O)C(c1cc2c(cc1Cl)OCO2)c1c[nH]c2cc(Br)ccc12 | null | null | null |
895,415 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.C([Mg]Cl)(C)C.[C:15]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=[O:21])#[N:16]>C1COCC1>[OH:21][CH:20]([C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1)[C:19]1[CH:18]=[C:17]([CH:24]=[CH:23][CH:22]=1)[C:15]#[N:16] | N#Cc1cccc(C=O)c1 | CSc1nccc(I)n1 | null | CC(C)[Mg]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 | null | 1 | To the solution of 4-iodo-2-(methylthio)pyrimidine (2.52 g, 10 mmol) in THF (50 mL) at 0 ° C. was added i-PrMgCl (5 mL, 2.0 M, 10 mmol) and stirred for 1 h. 3-cyanobenzaldehyde (1.31 g, 10 mmol) was added. The mixture was stirred at 0° C. for 2 h. The reaction was quenched with saturated aqueous NH4Cl solution and extr... | CSc1nccc(C(O)c2cccc(C#N)c2)n1 | null | null | null |
853,272 | ord_dataset-faa0236be76c4501841c954527cd1b6c | null | 2008-01-01T00:12:00 | true | [C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH2:31][C:32]1[C:33]2[N:34]([C:38]([CH:57]3[CH2:60][CH2:59][CH2:58]3)=[N:39][C:40]=2[C:41]2[CH:42]=[C:43]([CH:54]=[CH:55][CH:56]=2)[O:44][CH2:45][C:46]2[CH:47]=[C:48]([CH2:52]O)[CH:49]=[CH:50][CH:51]=2)[C... | Nc1nccn2c(C3CCC3)nc(-c3cccc(OCc4cccc(CO)c4)c3)c12 | O=C1NC(=O)c2ccccc21 | null | CC(C)OC(=O)/N=N/C(=O)OC(C)C | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 24 | Phthalimide (44 mg, 0.25 mmol), PS-triphenylphosphine (169 mg, 0.37 mmol) and {3-[3-(8-Amino-3-cyclobutyl-imidazo[1,5-a]pyrazin-1-yl)-phenoxymethyl]-phenyl}-methanol (100 mg, 0.25 mmol) were added to a dry rbf and dissolved with THF (1.25 mL), which was then evacuated and purged three times with nitrogen. DIAD (61 mg, ... | Nc1nccn2c(C3CCC3)nc(-c3cccc(OCc4cccc(CN5C(=O)c6ccccc6C5=O)c4)c3)c12 | null | null | null |
1,600,691 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([NH:26][CH:27]([CH3:31])[CH2:28][O:29][CH3:30])=[C:12]([NH:17][C:18]([CH:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=O)[CH:13]=[N:14]3)=[CH:9][C:8]=2[O:32][CH3:33])=[C:5]([CH3:34])[O:4][N:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH3:33][... | COCC(C)Nc1c(NC(=O)C2CCOCC2)cnc2cc(-c3c(C)noc3C)c(OC)cc12 | null | null | Cc1ccc(S(=O)(=O)O)cc1 | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | O | null | null | null | null | null | null | null | null | null | null | null | A mixture of N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-4-((1-methoxypropan-2-yl)amino)quinolin-3-yl)tetrahydro-2H-pyran-4-carboxamide (for a preparation see Intermediate 3) (11.95 g, 25.5 mmol) and p-toluenesulfonic acid (1.2 g, 25.5 mmol) in toluene (250 ml) was heated under nitrogen at reflux using a Dean-Stark appa... | COCC(C)n1c(C2CCOCC2)nc2cnc3cc(-c4c(C)noc4C)c(OC)cc3c21 | null | null | null |
564,654 | ord_dataset-5c8a417a8ba04cf0b7f78b9db9af1d01 | null | 2002-01-01T00:10:00 | true | C([O:8][C:9]([CH:11]([CH3:38])[CH2:12][P:13]([CH2:20][CH:21]([CH2:29][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:10])C1C=CC=CC=1>[Pd].C(OCC)(=O)C>[C:9]([CH:11]([CH3:38])[CH2:12][P:13]([CH2:2... | CC(CP(=O)(CC(CCC(=O)OC(C)(C)C)C(=O)OC(C)(C)C)OC(C)(C)C)C(=O)OCc1ccccc1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | A solution of di-tert-butyl 2-[[[2-(benzyl-carboxy)propyl]tert-butoxyphosphinyl]methyl]pentane-1,5-dioate (8.9 g, 16.1 mmol), palladium on carbon catalyst (10%, 1.0 g) and ethyl acetate (100 ml) was shaken under hydrogen (60 psi) for 16 hours. The reaction mixture was filtered over celite and the filtrate was concentra... | CC(CP(=O)(CC(CCC(=O)OC(C)(C)C)C(=O)OC(C)(C)C)OC(C)(C)C)C(=O)O | null | 100.3 | null |
810,509 | ord_dataset-da49b0378abf41bf92ab8ecdd3feb28b | null | 2008-01-01T00:02:00 | true | N[C@@H:2]([CH:6](C)C)[C@H:3](O)[CH3:4].[NH2:9][C@H:10]([C@H:14]([OH:19])[CH2:15][CH2:16][CH2:17][CH3:18])[CH:11]([CH3:13])[CH3:12]>>[CH3:12][CH:11]([C@H:10]([N:9]1[CH2:4][CH2:3][CH2:2][CH2:6]1)[C@H:14]([OH:19])[CH2:15][CH2:16][CH2:17][CH3:18])[CH3:13] | CC(C)[C@H](N)[C@@H](C)O | CCCC[C@@H](O)[C@@H](N)C(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Repeat Step (a) of EXAMPLE 1, but (2R,3S)-3-amino-4-methyl pentan-2-ol is replaced with (3S,4R)-3-amino-2-methyloctan-4-ol. The analysis for compound | CCCC[C@@H](O)[C@H](C(C)C)N1CCCC1 | null | null | null |
1,456,876 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [CH2:1]([O:8][C:9]1[C:10]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[N:11][C:12]([CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][C:32]([CH2:35][O:36][Si](C(C)(C)C)(C)C)=[CH:31][CH:30]=4)=[CH:25][CH:24]=3)[CH2:19][CH2:18]2)=[N:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH... | Cc1nc(CC2CCN(c3ccc(-c4ccc(CO[Si](C)(C)C(C)(C)C)cc4)cc3)CC2)nc(C(=O)OC(C)(C)C)c1OCc1ccccc1 | null | null | Cl | O=C([O-])O | [Na+] | 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 | 1.5 | tert-Butyl 5-(benzyloxy)-2-{(1-[4′-({[tert-butyl(dimethyl)silyl]oxy}methyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylate (0.98 g, 1.4 mmol) was dissolved in 1,4-dioxane (10 mL), and a solution of hydrogen chloride in dioxane (4 M, 1.0 mL, 4 mmol) was added, followed by stirring at room temperatu... | Cc1nc(CC2CCN(c3ccc(-c4ccc(CO)cc4)cc3)CC2)nc(C(=O)OC(C)(C)C)c1OCc1ccccc1 | null | 100 | null |
36,742 | ord_dataset-3e699bae9dce4a0f996c34a7c5a4b79a | null | 1978-01-01T00:02:00 | true | [CH2:1]([S:8][CH2:9][CH2:10][NH:11][C:12]([NH2:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:15]O>C(O)=O>[CH2:1]([S:8]([CH2:9][CH2:10][NH:11][C:12]([NH2:14])=[O:13])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | OO | NC(=O)NCCSCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=CO | null | null | null | null | null | null | null | null | null | null | 30 | 2 | To a solution of 2-benzylthio ethylurea (0.03 mole) in 12 ml of formic acid, there are added 3 ml of H2O2 (110 volumes). The resulting solution is agitated for 2 hours while maintaining the temperature at 30° C. The solution is then concentrated under reduced pressure and the resulting oil residue, taken up in sulfuric... | NC(=O)NCCS(=O)Cc1ccccc1 | null | null | null |
462,013 | ord_dataset-5ca9db262dd24c5a9315cdc8ef055b7e | null | 2000-01-01T00:04:00 | true | [CH3:1][O:2][C:3](=[O:17])[CH2:4][O:5][C:6]1[C:11]([F:12])=[CH:10][C:9]([N+:13]([O-])=O)=[CH:8][C:7]=1[F:16].[H][H]>[Pd].O1CCCC1>[CH3:1][O:2][C:3](=[O:17])[CH2:4][O:5][C:6]1[C:7]([F:16])=[CH:8][C:9]([NH2:13])=[CH:10][C:11]=1[F:12] | [H][H] | COC(=O)COc1c(F)cc([N+](=O)[O-])cc1F | null | [Pd] | 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 | null | null | A slurry of (4-nitro-2,6-difluoro-phenoxy)-acetic acid methyl ester (737 mg, 2.98 mmol) and 10% palladium on carbon (200 mg) in tetrahydrofuran (40 mL) was stirred under 1 atmosphere of hydrogen gas for 7 h. The mixture was flushed with nitrogen, and filtered through a pad of celite to afford the title compound as a pa... | COC(=O)COc1c(F)cc(N)cc1F | null | 99.8 | null |
255,208 | ord_dataset-30ad5cf6083a45a387b45bebad1a4d65 | null | 1992-01-01T00:10:00 | true | [C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[Cl-].[Al+3].[Cl-].[Cl-].[C:12]([O:15][CH:16]([CH3:24])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:14])[CH3:13].O>ClCCCl>[C:12]([O:15][CH:16]([CH3:24])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:4]([CH2:3][CH2:2][C:1]([OH:6])=[O:7])=[O:5])=[CH:20][CH:19]=1)(=[... | O=C1CCC(=O)O1 | CC(=O)OC(C)Cc1ccccc1 | null | [Al+3] | [Cl-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCCl | O | null | null | null | null | null | null | null | null | null | 25 | 0.25 | Succinic anhydride (3 g) was added, under a nitrogen atmosphere, to a stirred slurry of aluminium chloride (8.25 g) in 1,2-dichloroethane (50 ml). The resulting mixture was stirred at room temperature for 15 minutes. A solution of 2-acetoxypropyl benzene (5 g) in 1,2-dichloroethane (20 ml) was added, dropwise, to the s... | CC(=O)OC(C)Cc1ccc(C(=O)CCC(=O)O)cc1 | null | null | null |
592,175 | ord_dataset-7a74d48eeefd45aba53e7258f3ae067a | null | 2003-01-01T00:04:00 | true | [C:1](Cl)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[N+:9]([C:12]1[CH:38]=[CH:37][C:15]([CH2:16][O:17][C:18]2[CH:19]=[C:20]([CH:34]=[CH:35][CH:36]=2)[C:21]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[S:30](=[O:33])(=[O:32])[NH2:31])=[O:22])=[CH:14][CH:13]=1)([O-:11])=[O:10]>CN(C)C1C=CN=CC=1.O1CCCC1>[N+:9]([C:... | NS(=O)(=O)c1ccccc1NC(=O)c1cccc(OCc2ccc([N+](=O)[O-])cc2)c1 | CCCCCC(=O)Cl | null | CN(C)c1ccncc1 | 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 | 1 | In a stream of nitrogen and at 0° C., 0.11 ml (0.80 mmol) of hexanoyl chloride was added to an anhydrous tetrahydrofuran (10 ml) solution containing 300 mg (0.07 mmol) of 3-(4-nitrobenzyloxy)-N-(2-sulfamoylphenyl)benzamide produced in Reference Example 5 and 171 mg (1.40 mmol) of 4-dimethylaminopyridine, the mixture wa... | CCCCCC(=O)NS(=O)(=O)c1ccccc1NC(=O)c1cccc(OCc2ccc([N+](=O)[O-])cc2)c1 | null | 869.8 | null |
1,215,069 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][O:5][C:6](=[O:21])[NH:7][C:8]1[CH:9]=[N:10][N:11]([CH2:13][C:14]2[O:15][C:16]([CH:19]=[O:20])=[CH:17][CH:18]=2)[CH:12]=1.[CH3:26][Mg]Br>>[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][O:5][C:6](=[O:21])[NH:7][C:8]1[CH:9]=[N:10][N:11]([CH2:13][C:14]2[O:1... | O=Cc1ccc(Cn2cc(NC(=O)OCc3ccccc3Cl)cn2)o1 | C[Mg]Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following general procedures G and H, starting from [1-(5-formyl-furan-2-ylmethyl)-1H-pyrazol-4-yl]-carbamic acid 2-chloro-benzyl ester and methylmagnesium bromide. | CC(=O)c1ccc(Cn2cc(NC(=O)OCc3ccccc3Cl)cn2)o1 | null | null | null |
323,846 | ord_dataset-24ad29d930104afea313b6c3bd11099e | null | 1996-01-01T00:01:00 | true | [CH2:1]=[C:2]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].Cl.[CH2:21]([N:23]([CH2:27][CH3:28])[CH2:24][CH2:25][SH:26])[CH3:22].N1CCCCC1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>CO>[CH2:21]([N:23]([CH2:27][CH3:28])[CH2:24][CH2:25][S:26][CH2:1][CH:2](... | C=C(Cc1ccccc1)C(=O)OCc1ccccc1 | CCN(CC)CCS | null | C[N+](C)(C)Cc1ccccc1 | Cl | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCNCC1 | CO | null | null | null | null | null | null | null | null | null | 25 | 16 | The oil prepared in Step 10 (1.5 g, 5.95 mmol) is dissolved under argon in methanol (22 mL). To this solution is added 2-diethylaminoethanethiol hydrochloride (1 g, 5.95 mmol), piperidine (0.78 mL, 7.85 mmol) and benzyltrimethylammonium hydroxide (0.25 mL, 0.6 mmol) , and the mixture is stirred at room temperature for ... | CCN(CC)CCSCC(Cc1ccccc1)C(=O)OCc1ccccc1 | null | null | null |
428,927 | ord_dataset-8cce6f317d644b348a7978a2dce3ea01 | null | 1999-01-01T00:03:00 | true | [NH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)=[O:5].[O:18]=[C:19]1[O:23][CH:22]([C:24](Cl)=[O:25])[CH2:21][CH2:20]1>>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([C:4](=[O:5])[C:3]2[CH:14]=[CH:15][CH:16]=[CH:17][C:2]=2[NH:1][C:24]([CH:22]2[CH2:21][CH2:20]... | O=C1CCC(C(=O)Cl)O1 | COc1ccc(C(=O)c2ccccc2N)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 | In substantially the same manner as in Example 8 (1), 8 g of 2-amino-4'-methoxybenzophenone was allowed to react with 5-oxotetrahydrofuran-2-carbonyl chloride to give 12 g of 4'-methoxy-2-(5-oxotetrahydrofuran-2-carbonyl)aminobenzophenone as an oily product. | COc1ccc(C(=O)c2ccccc2NC(=O)C2CCC(=O)O2)cc1 | null | null | null |
1,281,767 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [CH3:1][O:2][CH2:3][C@H:4]([CH3:38])[O:5][C:6]1[CH:7]=[C:8]([C:23]2[NH:27][C:26]([C:28]([O:30]CC3C=CC=CC=3)=[O:29])=[CH:25][CH:24]=2)[CH:9]=[C:10]([O:12][Si:13]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])[CH:11]=1>C(O)C.[C].[Pd]>[CH3:1][O:2][CH2:3][C@H:4]([CH3:38])[O:5][C:6]1[CH:7]=[... | COC[C@H](C)Oc1cc(O[Si](C(C)C)(C(C)C)C(C)C)cc(-c2ccc(C(=O)OCc3ccccc3)[nH]2)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 | null | 2 | Benzyl 5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[(triisopropylsilyl)oxy]phenyl}-1H-pyrrole-2-carboxylate (34.40 g, 64.0 mmol) synthesized in Example (106b) was dissolved in ethanol (320 mL), and a 10% palladium carbon catalyst (3.54 g) was added, followed by stirring for 2 hours under hydrogen atmosphere. The palladium c... | COC[C@H](C)Oc1cc(O[Si](C(C)C)(C(C)C)C(C)C)cc(-c2ccc(C(=O)O)[nH]2)c1 | null | 95.3 | null |
1,021,860 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | [NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:16][C:17]1[C:22]([C:23]([O:26][C:27](=[O:29])[CH3:28])([CH3:25])[CH3:24])=[CH:21][CH:20]=[CH:19][N:18]=1)[CH2:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[CH:10][N:9]=1.C[Si]([N:34]=[C:35]=[O:36])(C)C>CC(O)C>[CH3:14][C:13]1[C:8]([CH2:7][N:6]([CH2:16][C:17]2[C:22]([C:23... | C[Si](C)(C)N=C=O | CC(=O)OC(C)(C)c1cccnc1CN(CCCCN)Cc1ncc(C)cc1C | null | null | null | 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 | null | null | A solution of acetic acid 1-(2-{[(4-amino-butyl)-(3,5-dimethyl-pyridin-2-ylmethyl)-amino]-methyl}-pyridin-3-yl)-1-methyl-ethyl ester (223 mg, 0.56 mmol) in i-PrOH (3.7 mL) and treated with trimethylsilylisocyanate (110 μL, 0.78 mmol) at room temperature for 16 hours. The solution was then concentrated under reduced pre... | CC(=O)OC(C)(C)c1cccnc1CN(CCCCNC(N)=O)Cc1ncc(C)cc1C | null | 91.8 | null |
829,097 | ord_dataset-47bd90bf5ec74fcd99ce250a56e18c8f | null | 2008-01-01T00:07:00 | true | [CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH:13](=[O:17])[CH:14]([CH3:16])[CH3:15]>>[CH3:15][CH:14]([CH3:16])[CH:13]([C:12]1[N:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)[N:9]=[CH:10][CH:11]=1)[OH:17] | Cc1ccc(-n2cccn2)cc1 | CC(C)C=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 | This compound was prepared from 1-(4-methylphenyl)-1H-pyrazole (Tetrahedron Lett. 39(19): 2941 (1998)) and isobutyraldehyde using the method described in example 10B and isolated as a clear oil in 54% yield. | Cc1ccc(-n2nccc2C(O)C(C)C)cc1 | null | 54 | null |
297,018 | ord_dataset-ec7cb3d5a8704f64b01d401ea555974f | null | 1994-01-01T00:09:00 | true | C1(C2[O:12][CH2:11][CH:10]([O:13][C:14]([C:16]3[N:17]=[CH:18][C:19]4[NH:20][C:21]5[C:26]([C:27]=4[C:28]=3[CH2:29][O:30][CH3:31])=[CH:25][C:24]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[CH:23][CH:22]=5)=[O:15])[CH2:9][O:8]2)C=CC=CC=1>Cl>[OH:8][CH2:9][CH:10]([O:13][C:14]([C:16]1[N:17]=[CH:18][C:19]2[... | COCc1c(C(=O)OC2COC(c3ccccc3)OC2)ncc2[nH]c3ccc(OCc4ccccc4)cc3c12 | 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 | null | null | 135 mg of 6-benzyloxy-4-methoxymethyl-β-carboline-3carboxylic acid-(2-phenyl-1,3-dioxan-5-yl)-ester under 10 ml of acetone and 100 ml of 4N hydrochloric acid is stirred for 1 hour at 80° C. bath temperature. The batch is concentrated by evaporation, taken up in aqueous ammonia and suctioned off. 100 mg of 6-benzyloxy-4... | COCc1c(C(=O)OC(CO)CO)ncc2[nH]c3ccc(OCc4ccccc4)cc3c12 | null | 89 | null |
1,531,416 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]3([CH3:17])[O:16][CH2:15][CH2:14][O:13]3)=[CH:8][C:7]=2[C:18]2[C:19]3[N:26]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:25]([CH3:35])=[C:24]([C:36](O)=[O:37])[C:20]=3[N:21]=[CH:22][N:23]=2)[CH2:3][CH2:2]1.[NH2:39][CH:40]1[CH2:45][CH2:44][N:43... | CC(C)(C)OC(=O)N1CCC(N)CC1 | Cc1c(C(=O)O)c2ncnc(-c3cc(C4(C)OCCO4)ccc3OCC3CC3)c2n1COCC[Si](C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Starting from 4-[2-(cyclopropylmethoxy)-5-(2-methyl-1,3-dioxolan-2-yl)phenyl]-6-methyl-5-{[2-(trimethylsilyl)ethoxy]methyl}-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (example D.c13) and commercially available tert-butyl 4-amino-piperidine-1-carboxylate the title compound is obtained as pale yellow viscous oil. | Cc1c(C(=O)NC2CCN(C(=O)OC(C)(C)C)CC2)c2ncnc(-c3cc(C4(C)OCCO4)ccc3OCC3CC3)c2n1COCC[Si](C)(C)C | null | null | null |
240,857 | ord_dataset-685186618e9f4e7aaa72ac40c16ef354 | null | 1992-01-01T00:01:00 | true | Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1.Br[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1OC>>[CH:6]([C:5]1[CH:8]=[CH:9][CH:2]=[CH:3][C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH2:7] | C=Cc1ccc(Br)cc1 | COc1ccccc1Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A vinylbiphenyl polymer was prepared in the same manner as in Example 10 except that poly-p-bromostyrene obtained as in Example 10 by using p-bromostyrene instead of p-chlorostyrene, and o-bromoanisol were used. The polymer gave a peak of OCH3 through 1H-NMR measurement in the same manner as in Example 10. | C=Cc1ccccc1-c1ccccc1 | null | null | null |
11,648 | ord_dataset-7c810806c4564bada4a9550135bbb06f | null | 1976-01-01T00:08:00 | true | [Na].[OH:2][N:3]=[C:4]([C:10]#[N:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14].C(=O)([O-])O.[Na+]>O.C(OCC)(=O)C>[CH2:16]([O:15][C:13]([O:2][N:3]=[C:4]([C:10]#[N:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:14])[CH:17]=[CH2:18] | C=CCOC(=O)Cl | CCOC(=O)C(C#N)=NO | null | O=C([O-])O | [Na+] | [Na] | 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 | null | 1 | To a solution of sodium salt of ethyl 2-hydroxyimino-2-cyanoacetate (23.1 g) in water (100 ml), a solution of allyl chloroformate (17.0 g) in ethyl acetate (30 ml) is dropwise added at 5° to 10°C. The resulting mixture is stirred for 1 hour while adjusting pH to 7 with the addition of an aqueous solution of sodium hydr... | C=CCOC(=O)ON=C(C#N)C(=O)OCC | null | 62.4 | null |
1,721,739 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [F:1][C@H:2]1[C@H:8]([NH:9]C(=O)OC(C)(C)C)[CH2:7][CH2:6][C@@H:5]([C:17]2[N:21]([CH3:22])[N:20]=[CH:19][C:18]=2[N+:23]([O-])=O)[O:4][CH2:3]1.[F:26][C:27]1[CH:32]=[C:31]([CH2:33][O:34][CH3:35])[CH:30]=[C:29]([F:36])[C:28]=1[C:37]1[N:42]=[C:41]([C:43](O)=[O:44])[CH:40]=[CH:39][C:38]=1[F:46]>>[NH2:9][C@H:8]1[C@H:2]([F:1])[... | COCc1cc(F)c(-c2nc(C(=O)O)ccc2F)c(F)c1 | Cn1ncc([N+](=O)[O-])c1[C@@H]1CC[C@@H](NC(=O)OC(C)(C)C)[C@H](F)CO1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following the procedure for Example 111 starting from tert-butyl ((3S,4R,7S)-3-fluoro-7-(1-methyl-4-nitro-1H-pyrazol-5-yl)oxepan-4-yl)carbamate (Intermediate 80), and replacing 5-((tert-butoxycarbonyl)amino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acid with 6-(2,6-difluoro-4-(methoxymethyl)phenyl)-5-fluoropicolinic... | COCc1cc(F)c(-c2nc(C(=O)Nc3cnn(C)c3[C@@H]3CC[C@@H](N)[C@H](F)CO3)ccc2F)c(F)c1 | null | null | null |
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