Trifluoroacetic acid → 5-Amino-N-[4-(3-amino-3-methylpiperidin-1-yl)-6,7-dihydro-5H-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide

HRID 1499548노트

반응식

HRID 1499548 반응식
C(OC([NH:8][C:9]1[S:13][C:12]([C:14]2[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=2[F:21])=[N:11][C:10]=1[C:22]([NH:24][C:25]1[C:26]([N:34]2[CH2:39][CH2:38][CH2:37][C:36]([NH:41]C(=O)OC(C)(C)C)([CH3:40])[CH2:35]2)=[C:27]2[CH2:33][CH2:32][CH2:31][C:28]2=[N:29][CH:30]=1)=[O:23])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C:9]1[S:13][C:12]([C:14]2[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=2[F:21])=[N:11][C:10]=1[C:22]([NH:24][C:25]1[C:26]([N:34]2[CH2:39][CH2:38][CH2:37][C:36]([NH2:41])([CH3:40])[CH2:35]2)=[C:27]2[CH2:33][CH2:32][CH2:31][C:28]2=[N:29][CH:30]=1)=[O:23]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86726778tert-Butyl {1-[3-({[5-[(tert-butoxycarbonyl)amino]-2-(2,6-difluorophenyl)-1,3-thiazol-4-yl]carbonyl}amino)-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl]-3-methylpiperidin-3-yl}carbamate

생성물 1

HCID 867267795-Amino-N-[4-(3-amino-3-methylpiperidin-1-yl)-6,7-dihydro-5H-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide수율 60.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of tert-butyl {1-[3-({[5-[(tert-butoxycarbonyl)amino]-2-(2,6-difluorophenyl)-1,3-thiazol-4-yl]carbonyl}amino)-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl]-3-methylpiperidin-3-yl}carbamate (8.4 mg, 0.012 mmol), DCM (0.12 mL) and TFA (0.12 mL, 1.6 mmol) was stirred at room temperature for 30 min. The solution was then concentrated under reduced pressure and the residue was diluted with MeOH, filtered and purified by preparative LC-MS (XBridge™ preparative C18 5 μm OBD™ column, 30×10 mm, 60 mL/min., eluting with a gradient of MeCN and water with 0.1% NH4OH) to give the title compound as a white powder (3.5 mg, 59%). LCMS calc. for C24H27F2N6OS (M+H)+: m/z=485.2. Found: 485.2.

후처리

  1. concentrationThe solution was then concentrated under reduced pressure
  2. additionthe residue was diluted with MeOH
  3. filtrationfiltered
  4. custompurified by preparative LC-MS (XBridge™ preparative C18 5 μm OBD™ column, 30×10 mm, 60 mL/min.
  5. washeluting with a gradient of MeCN and water with 0.1% NH4OH)

출처 및 근거

ORD 기록
ord-f32bb0588c714c248bdf46c9b285e95a
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09200004B2

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