Ammonium Chloride → HCID 178427336, compound

HRID 2174038Notes

Reaction equation

HRID 2174038 reaction equation
[BH4-].[Na+].[C:3]([C:5]1[CH:40]=[CH:39][C:8]2[NH:9][C:10]([CH:12]([C:18]3[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[C:23]4[C:19]=3[CH:20]=[CH:21][N:22]4[S:29]([C:32]3[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=3)(=[O:31])=[O:30])[C:13](OCC)=[O:14])=[N:11][C:7]=2[CH:6]=1)#[N:4].[NH4+].[Cl-]>CO>[CH3:27][C:26]1[C:18]([CH:12]([C:10]2[NH:9][C:8]3[CH:39]=[CH:40][C:5]([C:3]#[N:4])=[CH:6][C:7]=3[N:11]=2)[CH2:13][OH:14])=[C:19]2[C:23](=[C:24]([CH3:28])[CH:25]=1)[N:22]([S:29]([C:32]1[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=1)(=[O:31])=[O:30])[CH:21]=[CH:20]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydride2×HCID 178470773HCID 178470773, compound

Product 1

HCID 178427336HCID 178427336, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (518 mg, 13.7 mmol) was added to a solution of (±)-ethyl 2-(5-cyano-1H-benzo[d]imidazol-2-yl)-2-(5,7-dimethyl-1-tosyl-1H-indol-4-yl)acetate (481 mg, 0.913 mmol) in MeOH (10 mL) at 23° C. The mixture was stirred at room temperature for 2 h. An additional aliquot of NaBH4 (1.03 g, 27.4 mmol) was added to the mixture. After 1 hr, sat. aq. NH4Cl was added and the resulting mixture was separated. The aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated. The residue was purified by silica gel chromatography (0-100% EtOAc in heptane) to provide the title compound. MS (ESI+) m/z 485.2 (M+H).

Workup

  1. waitAfter 1 hr
  2. customthe resulting mixture was separated
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (0-100% EtOAc in heptane)

Sources & evidence

ORD record
ord-c57add621a464ec8b5312fd3816fa3ab
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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