Diisopropylethylamine → (S)-N-(1-(cyclopropylsulfonyl)piperidin-3-yl)-6-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)benzo[d]thiazol-2-amine

HRID 1988447

반응식

HRID 1988447 반응식
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:29]=[CH:28][C:17]4[N:18]=[C:19]([NH:21][C@H:22]5[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]5)[S:20][C:16]=4[CH:15]=3)[CH:10]=[CH:9][N:8]=2)[CH:4]=[N:3]1.CCN(C(C)C)C(C)C.[CH:39]1([S:42](Cl)(=[O:44])=[O:43])[CH2:41][CH2:40]1>CN1C(=O)CCC1>[CH:39]1([S:42]([N:24]2[CH2:25][CH2:26][CH2:27][C@H:22]([NH:21][C:19]3[S:20][C:16]4[CH:15]=[C:14]([O:13][C:11]5[CH:10]=[CH:9][N:8]=[C:7]([C:5]6[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=6)[CH:12]=5)[CH:29]=[CH:28][C:17]=4[N:18]=3)[CH2:23]2)(=[O:44])=[O:43])[CH2:41][CH2:40]1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 2760919Cyclopropanesulfonyl chlorideHCID 57725571(S)-6-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)-N-(piperidin-3-yl)benzo[d]thiazol-2-amine

생성물 1

HCID 57725553(S)-N-(1-(cyclopropylsulfonyl)piperidin-3-yl)-6-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)benzo[d]thiazol-2-amine수율 66.7%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

To the solution of (S)-6-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)-N-(piperidin-3-yl)benzo[d]thiazol-2-amine (7.6 mg, 18 μmol) and DIPEA (35 μL, 200 μmol) in 400 μL of NMP was added cyclopropanesulfonyl chloride (10 mg, 98 μmol). The reaction solution was stirred at 55 for 16 hours. The crude reaction solution was purified on prep HPLC and evaporated in vacuo to give (S)—N-(1-(cyclopropylsulfonyl)piperidin-3-yl)-6-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)benzo[d]thiazol-2-amine (6.2 mg, 12 μmol) as white powder. ES/MS m/z 511.2 (MH+).

후처리

  1. customThe crude reaction solution
  2. customwas purified on prep HPLC
  3. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-57f3c0a0483740ff9c04dc4f10ae2713
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07553854B2

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