Hydrochloric Acid → HCID 58305611, compound

HRID 2362237Notes

Reaction equation

HRID 2362237 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:16]([C:17]4[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][C:18]=4[CH3:25])[C:15]([CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:14][CH:13]=3)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[BH4-].[Na+].Cl>CO>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([C:12]3[N:16]([C:17]4[CH:22]=[CH:21][C:20]([CH2:23][NH2:24])=[CH:19][C:18]=4[CH3:25])[C:15]([CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:14][CH:13]=3)=[CH:10][CH:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 58305696HCID 58305696, compound

Product 1

HCID 58305611HCID 58305611, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 3-(5-(4-(1H-imidazol-1-yl)phenyl)-1-(4-cyano-2-methylphenyl)-1H-pyrrol-2-yl)propanoate (30B) (300 mg, 0.71 mmol) in methanol (10 mL) was added CoCl2.6H2O (337 mg, 1.41 mmol), then NaBH4 (137 mg, 3.53 mmol) was added in portions within 30 min. The reaction mixture was stirred at room temperature for 2 h. 10% hydrochloric acid was added to adjust pH=2. After methanol was distilled, conc. NH3.H2O was added to adjust pH=8 followed by extraction with ethyl acetate (80 mL×3). The combined organic layers were dried over Na2SO4, filtered and concentrated to afford crude ethyl 3-(5-(4-(1H-imidazol-1-yl)phenyl)-1-(4-(aminomethyl)-2-methylphenyl)-1H-pyrrol-2-yl)propanoate (30C) (300 mg), which was used for the next step without further purification. LC-MS: [M+H]+ 428.

Workup

  1. distillationAfter methanol was distilled
  2. additionconc. NH3.H2O was added
  3. extractionfollowed by extraction with ethyl acetate (80 mL×3)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-666d25b23b7b4b018ebbebf044e88d0b
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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