Diisopropylethylamine → N-(3-(2-fluorobenzyl)-3-formamidocyclohexyl)-3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxamide

HRID 530898Notes

Reaction equation

HRID 530898 reaction equation
[NH2:1][C:2]1([CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=2[F:53])[CH2:7][CH2:6][CH2:5][CH:4]([NH:8][C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:15]=[C:14]3[C:39]2[CH:44]=[CH:43][N:42]=[C:41]([CH3:45])[CH:40]=2)=[O:10])[CH2:3]1.[CH:54](OCC(F)(F)F)=[O:55].CCN(C(C)C)C(C)C>C1COCC1>[F:53][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=1[CH2:46][C:2]1([NH:1][CH:54]=[O:55])[CH2:7][CH2:6][CH2:5][CH:4]([NH:8][C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([C:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:15]=[C:14]3[C:39]2[CH:44]=[CH:43][N:42]=[C:41]([CH3:45])[CH:40]=2)=[O:10])[CH2:3]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1416812,2,2-Trifluoroethyl formateHCID 67983880N-(3-amino-3-(2-fluorobenzyl)cyclohexyl)-3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxamide

Product 1

HCID 86698252N-(3-(2-fluorobenzyl)-3-formamidocyclohexyl)-3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A reaction mixture of N-(3-amino-3-(2-fluorobenzyl)cyclohexyl)-3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxamide (0.01 mmol, 7 mg), 2,2,2-trifluoroethyl formate (0.06 mmol, 6 μL) and DIEA (10 equiv.) in THF was stirred at room temperature for overnight. The product, N-(3-(2-fluorobenzyl)-3-formamidocyclohexyl)-3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxamide, was obtained after evaporation of solvent.

Sources & evidence

ORD record
ord-00c3547fa3674639a424efe15495ec20
Source dataset
uspto-grants-2016_05
Patent number
US09351965B2

Reaction notes

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