Water → HCID 58902218, compound

HRID 1640190Notes

Reaction equation

HRID 1640190 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([NH:20][C:21]([CH:23]2[CH2:32][C:31]3[CH:30]=[C:29]([O:33][C:34]4[CH:39]=[CH:38][N:37]=[C:36]([C:40](OC)=[O:41])[CH:35]=4)[CH:28]=[CH:27][C:26]=3[CH2:25][CH2:24]2)=[O:22])[CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].O>CO>[OH:41][CH2:40][C:36]1[CH:35]=[C:34]([O:33][C:29]2[CH:30]=[C:31]3[C:26]([CH2:25][CH2:24][CH:23]([C:21]([NH:20][C:12]4[CH:11]=[C:10]([CH:15]=[C:14]([C:16]([F:19])([F:17])[F:18])[CH:13]=4)[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:22])[CH2:32]3)=[CH:27][CH:28]=2)[CH:39]=[CH:38][N:37]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 58902444HCID 58902444, compound

Product 1

HCID 58902218HCID 58902218, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-{[7-({[3-{[(tert-butoxycarbonyl)amino]methyl}-5-(trifluoromethyl)phenyl]amino}carbonyl)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}pyridine-2-carboxylate (1.03 g, 1.72 mmol) in MeOH (17 mL) at 0° C., was added sodium borohydride (0.39 g, 13.3 mmol) in small portions. The reaction mixture was allowed to warm slowly to rt and then allowed to stir for 18 h. Water was added and the precipitate which formed was filtered, washed with water and hexane and dried under vacuum to give tert-butyl [3-{[(7-{[2-(hydroxymethyl)pyridin-4-yl]oxy}-1,2,3,4-tetrahydronaphthalen-2-yl)carbonyl]amino}-5-(trifluoromethyl)benzyl]carbamate (913 mg, 93.0%) as a white solid. LCMS: (FA) ES+ 572.3, ES− 570.4.

Workup

  1. customthe precipitate which formed
  2. filtrationwas filtered
  3. washwashed with water and hexane
  4. customdried under vacuum

Sources & evidence

ORD record
ord-f4de1a8445c84e388be26b804d4fb01f
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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