Hydrogen Bromide → 3-Amino-N-{4-[(3S,5R)-3-amino-5-(trifluoromethyl)piperidin-1-yl]pyridin-3-yl}-7-(4-methylpiperazin-1-yl)quinoline-2-carboxamide

HRID 924464ノート

反応式

HRID 924464 の反応式
C(OC([NH:8][C@H:9]1[CH2:14][C@@H:13]([C:15]([F:18])([F:17])[F:16])[CH2:12][N:11]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][C:20]=2[NH:25][C:26]([C:28]2[C:37]([NH:38]C(=O)OCC3C=CC=CC=3)=[CH:36][C:35]3[C:30](=[CH:31][C:32]([N:49]4[CH2:54][CH2:53][N:52]([CH3:55])[CH2:51][CH2:50]4)=[CH:33][CH:34]=3)[N:29]=2)=[O:27])[CH2:10]1)=O)(C)(C)C.Br>CC(O)=O>[NH2:38][C:37]1[C:28]([C:26]([NH:25][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][C:19]=2[N:11]2[CH2:12][C@H:13]([C:15]([F:17])([F:18])[F:16])[CH2:14][C@H:9]([NH2:8])[CH2:10]2)=[O:27])=[N:29][C:30]2[C:35]([CH:36]=1)=[CH:34][CH:33]=[C:32]([N:49]1[CH2:54][CH2:53][N:52]([CH3:55])[CH2:51][CH2:50]1)[CH:31]=2

参加物

4

反応物 2

HCID 260Hydrogen BromideHCID 86726907Benzyl [2-[({4-[(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-(trifluoromethyl)piperidin-1-yl]pyridin-3-yl}amino)carbonyl]-7-(4-methylpiperazin-1-yl)quinolin-3-yl]carbamate

生成物 1

HCID 867269083-Amino-N-{4-[(3S,5R)-3-amino-5-(trifluoromethyl)piperidin-1-yl]pyridin-3-yl}-7-(4-methylpiperazin-1-yl)quinoline-2-carboxamide

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of benzyl [2-[({4-[(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-(trifluoromethyl)piperidin-1-yl]pyridin-3-yl}amino)carbonyl]-7-(4-methylpiperazin-1-yl)quinolin-3-yl]carbamate (0.006 g, 0.008 mmol) and 2 mL of 4.0 M HBr in AcOH was stirred at room temperature for 2 h. The mixture was concentrated under reduced pressure, and the residue was then treated with 4.5 mL of MeOH and 0.5 mL of NH4OH solution. The mixture was filtered and the filtrate was purified by preparative HPLC (XBridge™ C18 column, eluting with a gradient of MeCN/water containing 0.1% NH4OH, at a flow rate of 30 mL/min.) to afford the title compound. LCMS calc. for C26H32F3N8O [M+H]+: m/z=529.3. found: 529.3.

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionthe residue was then treated with 4.5 mL of MeOH and 0.5 mL of NH4OH solution
  3. filtrationThe mixture was filtered
  4. customthe filtrate was purified by preparative HPLC (XBridge™ C18 column
  5. washeluting with a gradient of MeCN/water containing 0.1% NH4OH, at a flow rate of 30 mL/min.)

出典と根拠

ORDレコード
ord-433119c22dac47329c3107980a1cb71e
出典データセット
uspto-grants-2016_03
特許番号
US09278950B2

反応ノート

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