Sodium borohydride → HCID 15952180, compound

HRID 2244246Notes

Reaction equation

HRID 2244246 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([N:18]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[CH2:22][N:21]3[C:29]([C:32]([NH:34][CH2:35][C:36]4[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=4)=[O:33])=[CH:30][CH:31]=[C:20]3[CH2:19]2)=[O:17])=[CH:12][C:11]=1[CH3:42])(=[O:3])[CH3:2].[BH4-].[Na+]>CC(O)C.O>[OH:3][CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([N:18]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[CH2:22][N:21]3[C:29]([C:32]([NH:34][CH2:35][C:36]4[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=4)=[O:33])=[CH:30][CH:31]=[C:20]3[CH2:19]2)=[O:17])=[CH:12][C:11]=1[CH3:42])[CH3:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 15951799HCID 15951799, compound

Product 1

HCID 15952180HCID 15952180, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

To a solution of 10-[(2′-acetyl-2-methyl-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 29 (0.122 g, 0.220 mmol) in 2-propanol (5 mL) and water (1 mL) was added sodium borohydride (0.0092 mg, 0.242 mmol) and the reaction mixture stirred at room temperature under nitrogen for 24 hours. The reaction was quenched by the addition of 2 M hydrochloric acid (10 mL) and then washed with diethyl ether (20 mL). The aqueous phase was basified by the addition of 2 M sodium hydroxide and the resulting milky suspension extracted with ethyl acetate ( 2×30 mL). The combined organic extracts were washed with water (50 mL) and brine (50 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford a colorless syrup. Purification by flash chromatography using a solvent gradient of 1 to 5% methanol in dichloromethane gave a colorless glass that was recrystallized from diethyl ether/hexane to afford the title compound (0.061 g, 50%) as white solid.

Workup

  1. customThe reaction was quenched by the addition of 2 M hydrochloric acid (10 mL)
  2. washwashed with diethyl ether (20 mL)
  3. additionThe aqueous phase was basified by the addition of 2 M sodium hydroxide
  4. extractionthe resulting milky suspension extracted with ethyl acetate ( 2×30 mL)
  5. washThe combined organic extracts were washed with water (50 mL) and brine (50 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto afford a colorless syrup
  9. customPurification by flash chromatography
  10. customgave a colorless glass that
  11. customwas recrystallized from diethyl ether/hexane

Sources & evidence

ORD record
ord-f7e2de7ab0e24ff4adf50a686f030479
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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