Triethylamine → Methanesulfonic acid 5-[(5-bromo-imidazo[1,2-a]pyrazin-8-yl)-tert-butoxycarbonyl-amino]-2-morpholin-4-yl-benzyl ester

HRID 1366224노트

반응식

HRID 1366224 반응식
[C:1]([O:5][C:6](=[O:32])[N:7]([C:22]1[C:23]2[N:24]([CH:29]=[CH:30][N:31]=2)[C:25]([Br:28])=[CH:26][N:27]=1)[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[C:10]([CH2:20][OH:21])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>C(Cl)Cl.C(OCC)(=O)C>[Br:28][C:25]1[N:24]2[CH:29]=[CH:30][N:31]=[C:23]2[C:22]([N:7]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:32])[C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)=[C:10]([CH:9]=2)[CH2:20][O:21][S:41]([CH3:40])(=[O:43])=[O:42])=[N:27][CH:26]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86652629(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(3-hydroxymethyl-4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester

생성물 1

HCID 86652630Methanesulfonic acid 5-[(5-bromo-imidazo[1,2-a]pyrazin-8-yl)-tert-butoxycarbonyl-amino]-2-morpholin-4-yl-benzyl ester수율 113.1%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

To a cooled solution (0° C.) of (5-bromo-imidazo[1,2-a]pyrazin-8-yl)-(3-hydroxymethyl-4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester (0.17 g, 0.34 mmol) in DCM (0.5 mL), is added triethylamine (0.104 mL, 0.74 mmol) followed by methanesulfonyl chloride (0.046 mL, 0.6 mmol). The reaction mixture is stirred at 0° C. for 1 hour and an additional hour at room temperature. The reaction mixture is diluted with ethyl acetate and washed with water. The organic layer is dried over MgSO4, filtered and concentrated in vacuo to give the title compound (0.224 g) used in the next step without further purification.

후처리

  1. washwashed with water
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-e2e7a2687d5a42ebbfb44b5f1d4f3c96
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893058B2

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