Hydrazine hydrate (1:1) → (1S,2S,5R)-(2-aminomethyl-7,7-difluoro-3-aza-bicyclo[3.3.0]-oct-3-yl)-(2-methyl-5-m-tolyl-thiazol-4-yl)-methanone

HRID 425807

반응식

HRID 425807 반응식
[CH3:1][C:2]1[S:3][C:4]([C:31]2[CH:32]=[C:33]([CH3:37])[CH:34]=[CH:35][CH:36]=2)=[C:5]([C:7]([N:9]2[CH2:16][C@H:15]3[C@H:11]([CH2:12][C:13]([F:18])([F:17])[CH2:14]3)[C@H:10]2[CH2:19][N:20]2C(=O)C3C(=CC=CC=3)C2=O)=[O:8])[N:6]=1.O.NN>CCO>[NH2:20][CH2:19][C@H:10]1[N:9]([C:7]([C:5]2[N:6]=[C:2]([CH3:1])[S:3][C:4]=2[C:31]2[CH:32]=[C:33]([CH3:37])[CH:34]=[CH:35][CH:36]=2)=[O:8])[CH2:16][C@H:15]2[C@@H:11]1[CH2:12][C:13]([F:18])([F:17])[CH2:14]2

참가 물질

4

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 66703707(1S,2S,5R)-2-[3-(2-methyl-5-m-tolyl-thiazole-4-carbonyl)-7,7-difluoro-3-azabicyclo[3.3.0]oct-2-ylmethyl)-isoindole-1,3-dione

생성물 1

HCID 59411607(1S,2S,5R)-(2-aminomethyl-7,7-difluoro-3-aza-bicyclo[3.3.0]-oct-3-yl)-(2-methyl-5-m-tolyl-thiazol-4-yl)-methanone수율 92.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of (1S,2S,5R)-2-[3-(2-methyl-5-m-tolyl-thiazole-4-carbonyl)-7,7-difluoro-3-azabicyclo[3.3.0]oct-2-ylmethyl)-isoindole-1,3-dione (130 mg), hydrazine monohydrate (0.078 mL) in EtOH (10 mL) was stirred at reflux for 1 h 45. After cooling to RT, the reaction mixture was concentrated in vacuo, dissolved in DCM, washed twice with water, brine, dried (MgSO4), filtered and concentrated to yield the title compound (90 mg, 92%) as a colorless oil which was used for the next step without further purification. LC-MS: tR=0.79 min; [M+H]+=392

후처리

  1. temperatureat reflux for 1 h 45
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. dissolutiondissolved in DCM
  4. washwashed twice with water, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7591001438a54518a6eb4305f0d71b60
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106215B2

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