Sodium borohydride → HCID 57435785, 화합물

HRID 30597노트

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HRID 30597 반응식
[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

참가 물질

3

반응물 2

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

생성물 1

HCID 57435785HCID 57435785, 화합물수율 94%

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fbfb19012be14ecda4ddb24618f6e670
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423158B2

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