Hydrochloric Acid → HCID 178459292, compound

HRID 2235435Notes

Reaction equation

HRID 2235435 reaction equation
[CH3:1][C:2]1([CH3:29])[C:10]2[CH:9]=[C:8]3[N:11]=[C:12]([NH:14][C:15](=[O:22])[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[NH:13][C:7]3=[CH:6][C:5]=2[N:4]([CH2:23][C:24](=[O:27])[CH2:25][CH3:26])[C:3]1=[O:28].[BH4-].[Na+].Cl>C(Cl)Cl.CO>[OH:27][CH:24]([CH2:25][CH3:26])[CH2:23][N:4]1[C:5]2[CH:6]=[C:7]3[NH:13][C:12]([NH:14][C:15](=[O:22])[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[N:11][C:8]3=[CH:9][C:10]=2[C:2]([CH3:1])([CH3:29])[C:3]1=[O:28]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 178459291HCID 178459291, compound

Product 1

HCID 178459292HCID 178459292, compoundYield 44.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a cooled solution (0° C.) of N-[7,7-dimethyl-6-oxo-5-(2-oxo-butyl)-3,5,6,7-tetrahydro-imidazo[4,5-f]indol-2-yl]-benzamide (150 mg) in CH2Cl2 (3.5 ml) and MeOH (1.5 ml) is added NaBH4 (29.1 mg; 0.77 mmol). The mixture is stirred and warmed to RT overnight. After completion hydrochloric acid (5 ml; 1 N) is added and the mixture extracted with EtOAc. The organic phase is washed with brine, dried over MgSO4 and evaporated to dryness to give N-[5-(2-hydroxy-butyl)-7,7-dimethyl-6-oxo-3,5,6,7-tetrahydro-imidazo[4,5-f]indol-2-yl]-benzamide (67 mg) as a racemic mixture.

Workup

  1. extractionthe mixture extracted with EtOAc
  2. washThe organic phase is washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-92a70a44b6414314a62e233b8733accf
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

Loading…