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 1499548ノート

反応式

HRID 1499548 の反応式
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]

参加物

4

反応物 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

生成物 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-carboxamide収率 60.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f32bb0588c714c248bdf46c9b285e95a
出典データセット
uspto-grants-2015_12
特許番号
US09200004B2

反応ノート

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