Sodium borohydride → HCID 57435785, compound

HRID 30597Notes

Reaction equation

HRID 30597 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH:27]([F:29])[F:28])=[CH:22][CH:21]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]3[CH2:18][C:17](=[O:19])[CH2:16]3)[CH:10]=2)[N:3]=1.[BH4-].[Na+]>>[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:20]2[CH:21]=[CH:22][C:23]([O:26][CH:27]([F:29])[F:28])=[CH:24][CH:25]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]3[CH2:16][CH:17]([OH:19])[CH2:18]3)[CH:10]=2)[N:3]=1

Participants

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 161134412-amino-5-[4-(difluoromethoxy)phenyl]-3-methyl-5-[3-(3-oxocyclobutyl)phenyl]-3,5-dihydro-4H-imidazol-4-one

Product 1

HCID 57435785HCID 57435785, compoundYield 94%

Conditions

Temperature
0 °C

Procedure

A methanolic solution of 2-amino-5-[4-(difluoromethoxy)phenyl]-3-methyl-5-[3-(3-oxocyclobutyl)phenyl]-3,5-dihydro-4H-imidazol-4-one (0.324 gm, 0.811 mmol) at ice bath temperatures was treated all at once with NaBH4 (0.042 gm, 1.11 mmol), stirred at 0° C. for 45 minutes and concentrated in vacuo. The solid residue was partitioned between water and chloroform. The organic phase was separated, dried over sodium sulfate and evaporated to a foam. This foam was dissolved in chloroform and precipitated with hexane to give the title compound as a white solid, 0.307 g (94% yield), mp 186-190° C.; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.70-1.86 (m, 2 H) 2.53-2.60 (m, 2 H) 2.70-2.85 (m, 1 H) 2.97 (s, 3 H) 3.89-4.08 (m, 1 H) 5.08 (t, J=5.2 Hz, 1 H) 6.69 (s, 2 H) 7.10 (d, J=8.6 Hz, 3 H) 7.17 (t, J=74.2 Hz, 1 H) 7.19-7.33 (m, 3 H) 7.45 (d, J=8.8 Hz, 2 H); MS (ES) m/z 400.2 [M−H]−; HRMS: calcd for C21H21F2N3O3+H+, 402.16237. found (ESI, [M+H]+), 402.1630.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe solid residue was partitioned between water and chloroform
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulfate
  5. customevaporated to a foam
  6. dissolutionThis foam was dissolved in chloroform
  7. customprecipitated with hexane

Sources & evidence

ORD record
ord-fbfb19012be14ecda4ddb24618f6e670
Source dataset
uspto-grants-2008_09
Patent number
US07423158B2

Reaction notes

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