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Ammonium Hydroxide → ((1S,2S)-4'-(4-Chlorophenyl)-2',3',9'-trimethylspiro[cyclo-propane-1,6'-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin]-2-yl)methanamine

HRID 1772340
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HRID 1772340 반응식
Br[CH2:2][C@H:3]1[C@@:5]2([N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[C:9]3[C:19]([CH3:23])=[C:20]([CH3:22])[S:21][C:8]=3[N:7]3[C:24]([CH3:27])=[N:25][N:26]=[C:6]23)[CH2:4]1.[OH-].[NH4+:29]>CN(C=O)C>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([C:10]2[C:9]3[C:19]([CH3:23])=[C:20]([CH3:22])[S:21][C:8]=3[N:7]3[C:24]([CH3:27])=[N:25][N:26]=[C:6]3[C@@:5]3([CH2:4][C@H:3]3[CH2:2][NH2:29])[N:11]=2)=[CH:17][CH:16]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 14923Ammonium HydroxideHCID 57404762(1S,2R)-2-(bromomethyl)-4'-(4-chlorophenyl)-2',3',9'-trimethylspiro-[cyclopropane-1,6'-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine]

생성물 1

HCID 57404936((1S,2S)-4'-(4-Chlorophenyl)-2',3',9'-trimethylspiro[cyclo-propane-1,6'-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin]-2-yl)methanamine수율 4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of (1S,2R)-2-(bromomethyl)-4′-(4-chlorophenyl)-2′,3′,9′-trimethylspiro-[cyclopropane-1,6′-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine](350 mg, 0.758 mmol) in DMF (4 mL) was added ammonium hydroxide (3 mL, 77 mmol) at rt. After 9 h at rt, silica gel was added, and the solvent was removed under vacuum. The dry silica gel was packed, and the product was purified by chromatography (Hexane/EtOAc 5:5 to 0:10 then DCM/MeOH 10:0 to 9:1). A second (EtOAc/toluene/MeOH 4:4:2) and a third chromatography were performed (2-propanol 100%) to give a tan solid (12 mg). LRMS (M+H)+: 398 m/z.

후처리

  1. additionsilica gel was added
  2. customthe solvent was removed under vacuum
  3. customthe product was purified by chromatography (Hexane/EtOAc 5:5 to 0:10

출처 및 근거

ORD 기록
ord-a1024bc598564ee2bd566a1b2e723279
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09249161B2

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