Sodium borohydride → HCID 18355175, compound

HRID 1533812Notes

Reaction equation

HRID 1533812 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:32]=[CH:33][C:34]=1[NH:35][C:36]([C:38]1[C:46]2[N:45]=[C:44]([CH2:47][NH:48][C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[NH:43][C:42]=2[CH:41]=[CH:40][CH:39]=1)=[O:37])[C:6]([N:8]([CH3:31])[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([N:24]1[CH2:29][CH2:28][C:27](=[O:30])[CH2:26][CH2:25]1)=[O:23])=[O:7].[BH4-].[Na+]>CO.C(Cl)(Cl)Cl>[OH:30][CH:27]1[CH2:26][CH2:25][N:24]([C:22]([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][O:16][C:10]2[CH:11]=[C:12]([CH3:15])[CH:13]=[CH:14][C:9]=2[N:8]([CH3:31])[C:6](=[O:7])[C:5]2[CH:32]=[CH:33][C:34]([NH:35][C:36]([C:38]3[C:46]4[N:45]=[C:44]([CH2:47][NH:48][C:49]([O:51][C:52]([CH3:53])([CH3:54])[CH3:55])=[O:50])[NH:43][C:42]=4[CH:41]=[CH:40][CH:39]=3)=[O:37])=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:23])[CH2:29][CH2:28]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 18354977HCID 18354977, compound

Product 1

HCID 18355175HCID 18355175, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-oxopiperidin-1-yl)carbonylpent-1-yloxy]phenyl]-4-[2-(tert-butoxycarbonyl)aminomethyl-1H-benzimidazol-4-yl]carbonylaminobenzamide (150 mg) in methanol (5 ml) was added sodium borohydride (7.52 mg) under an ice bath cooling and the mixture was stirred at the same temperature for 1 hour. The mixture was diluted with chloroform and the solution was washed with water and brine. The organic phase was dried over magnesium sulfate and the solvent was evaporated in vacuo to give N-[2-[5-(4-hydroxypiperidin-1-yl)carbonylpent-1-yloxy]-4-methylphenyl]-3-methoxy-N-methyl-4-[2-(tert-butoxycarbonyl)aminomethyl-1H-benzimidazol-4-yl]carbonylaminobenzamide (150 mg).

Workup

  1. temperaturecooling
  2. washthe solution was washed with water and brine
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-cc227f6815ac41ff9b5066ffea1a29a0
Source dataset
uspto-grants-2001_03
Patent number
US06207693B1

Reaction notes

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