Hydrochloric Acid → HCID 15952970, compound

HRID 2244243Notes

Reaction equation

HRID 2244243 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][N:20]3[C:28]([C:31]([NH:33][CH2:34][C:35]4[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=4)=[O:32])=[CH:29][CH:30]=[C:19]3[CH2:18]2)=[O:16])=[CH:11][CH:10]=1)=[O:2].[BH4-].[Na+].Cl>C(O)C>[OH:2][CH2:1][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[CH:11][C:12]([C:15]([N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][N:20]3[C:28]([C:31]([NH:33][CH2:34][C:35]4[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=4)=[O:32])=[CH:29][CH:30]=[C:19]3[CH2:18]2)=[O:16])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 15952274HCID 15952274, compound

Product 1

HCID 15952970HCID 15952970, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 10-[(2′-formyl-1,1′-biphenyl-4-yl)carbonyl]-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide of Example 567, Step B (0.75 mmole), in ethanol (5 mL) at 5° C. was treated with sodium borohydride (4.5 mmole). The mixture was stirred and allowed to warm to room temperature over 6 hours. To the reaction mixture was added 2N hydrochloric acid until a pH of 8.0 was reached. The ethanol was evaporated and the residue extracted with dichloromethane. The organic solutions were combined, dried over anhydrous sodium sulfate, and evaporated. The residue was purified by passing it through a short column of silica gel to give the title compound, m.p. 119-121° C.

Workup

  1. customThe ethanol was evaporated
  2. extractionthe residue extracted with dichloromethane
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe residue was purified

Sources & evidence

ORD record
ord-1084a85532dc4040b133f7dff4a95e56
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

Loading…