Sodium borohydride → HCID 58792273, compound

HRID 2220485Notes

Reaction equation

HRID 2220485 reaction equation
[NH2:1][C:2]1[N:3]([CH3:30])[C:4](=[O:29])[C:5]([C:20]2[CH:21]=[C:22]([CH:27]=[O:28])[N:23]([CH2:25][CH3:26])[CH:24]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]3[C:14]([F:19])=[N:15][CH:16]=[CH:17][CH:18]=3)[CH:8]=2)[N:6]=1.[BH4-].[Na+]>C1COCC1.CO>[NH2:1][C:2]1[N:3]([CH3:30])[C:4](=[O:29])[C:5]([C:20]2[CH:21]=[C:22]([CH2:27][OH:28])[N:23]([CH2:25][CH3:26])[CH:24]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]3[C:14]([F:19])=[N:15][CH:16]=[CH:17][CH:18]=3)[CH:8]=2)[N:6]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 15949563HCID 15949563, compound

Product 1

HCID 58792273HCID 58792273, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-{2-amino-4-[3-(2-fluoropyridin-3-yl)phenyl]-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl}-1-ethyl-1H-pyrrole-2-carbaldehyde (0.071 g; 0.25 mmol) in THF (20 mL) and methanol (5 mL) was stirred at ambient temperature as an excess of NaBH4 (0.071 g; 1.88 mmol) was added. After one hour the solvents were evaporated and the residue was taken up into dichloromethane and washed with water. The dichloromethane phase was dried over MgSO4, filtered, and evaporated. The resultant residue was crystallized from ethyl acetate and hexane to obtain the title product as a white solid, mp 170-172° C.; MS (ES) m/z 406.1; [M−H]−

Workup

  1. additionwas added
  2. customAfter one hour the solvents were evaporated
  3. washwashed with water
  4. dry with materialThe dichloromethane phase was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe resultant residue was crystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-e27f36afcbcb4472afc6c8b90ab6c97d
Source dataset
uspto-grants-2008_08
Patent number
US07417047B2

Reaction notes

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