Water → N-[(3RS)-1-{(3-azabicyclo[3.2.2]non-3-yl)-carbonylmethyl}-2,3-dihydro-5-(2-fluorophenyl)-2-oxo-1H-1,4-benzodiazepin-3-yl]-N'-(3-trifluoromethylphenyl)urea

HRID 963516

반응식

HRID 963516 반응식
[CH:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:10]([CH2:12][N:13]1[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[C:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])=[N:16][CH:15]([NH2:31])[C:14]1=[O:32])=[O:11])[CH2:2]2.[F:33][C:34]([F:55])([F:54])[C:35]1[CH:36]=[C:37]([NH:41][C:42](=O)[O:43]C2C=CC([N+]([O-])=O)=CC=2)[CH:38]=[CH:39][CH:40]=1.C(N(CC)CC)C.O>CN(C)C=O.C(OC(C)C)(C)C>[CH:5]12[CH2:8][CH2:9][CH:1]([CH2:7][CH2:6]1)[CH2:2][N:3]([C:10]([CH2:12][N:13]1[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[C:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])=[N:16][CH:15]([NH:31][C:42]([NH:41][C:37]3[CH:38]=[CH:39][CH:40]=[C:35]([C:34]([F:33])([F:54])[F:55])[CH:36]=3)=[O:43])[C:14]1=[O:32])=[O:11])[CH2:4]2

참가 물질

7

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 19081160(3RS)-1-{(3-azabicyclo[3.2.2]non-3-yl)-carbonylmethyl}-3-amino-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-oneHCID 190813254-nitrophenyl N-(3-trifluoromethylphenyl)carbamate

생성물 1

HCID 19081333N-[(3RS)-1-{(3-azabicyclo[3.2.2]non-3-yl)-carbonylmethyl}-2,3-dihydro-5-(2-fluorophenyl)-2-oxo-1H-1,4-benzodiazepin-3-yl]-N'-(3-trifluoromethylphenyl)urea수율 87%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 7914Diisopropyl Ether용매

실험 절차

To a solution of (3RS)-1-{(3-azabicyclo[3.2.2]non-3-yl)-carbonylmethyl}-3-amino-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one (100mg) and 4-nitrophenyl N-(3-trifluoromethylphenyl)carbamate (90.1 mg) in dimethylformamide (2 ml) was added triethylamine (28 mg) under stirring at ambient temperature. The mixture was stirred for 3.5 hours under the same condition. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water three times and dried over magnesium sulfate. The solvent was removed in vacuo to give an amorphous mass, which was pulverized in diisopropyl ether under vigorous stirring. The resulting powder was collected by filtration and washed with diisopropyl ether to afford N-[(3RS)-1-{(3-azabicyclo[3.2.2]non-3-yl)-carbonylmethyl}-2,3-dihydro-5-(2-fluorophenyl)-2-oxo-1H-1,4-benzodiazepin-3-yl]-N'-(3-trifluoromethylphenyl)urea (124.4 mg).

후처리

  1. stirringThe mixture was stirred for 3.5 hours under the same condition
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water three times
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customto give an amorphous mass, which
  7. filtrationThe resulting powder was collected by filtration
  8. washwashed with diisopropyl ether

출처 및 근거

ORD 기록
ord-ad7066b9110c45a18738f72280e621f7
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05763437

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