Sodium borohydride → HCID 58792273, compound

HRID 646271Notes

Reaction equation

HRID 646271 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-63a2d32910c94686be17ba93c682ef47
Source dataset
uspto-grants-2010_04
Patent number
US07705030B2

Reaction notes

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