Trifluoroacetic acid → 1-(Piperidin-4-yl)-1-[5-(3-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethanol

HRID 410518ノート

反応式

HRID 410518 の反応式
[OH:1][C:2]([CH:26]1[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]1)([C:4]1[S:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16]3[N:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][N:17]=3)[CH:10]=2)=[CH:7][N:8]=1)[CH3:3].C(O)(C(F)(F)F)=O>ClCCl>[NH:29]1[CH2:30][CH2:31][CH:26]([C:2]([C:4]2[S:5][C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16]4[N:21]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:19]=[CH:18][N:17]=4)[CH:10]=3)=[CH:7][N:8]=2)([OH:1])[CH3:3])[CH2:27][CH2:28]1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acid2 回HCID 67431059Tert-butyl 4-{1-hydroxy-1-[5-(3-{[4-(trifluoromethyl)-pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethyl}piperidine-1-carboxylate

生成物 1

HCID 672566901-(Piperidin-4-yl)-1-[5-(3-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethanol収率 54.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of the product of Step 4 (18.2 mg, 0.033 mmol) in dichloromethane (1 mL) was added TFA (1.00 mL, 12.98 mmol) and the mixture was stirred at room temperature. The solvent was removed by evaporation and stripped with ethyl acetate. The residue was concentrated and dried under high-vacuum to afford 1-(piperidin-4-yl)-1-[5-(3-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethanol (Example 15(2), 12.5 mg, 0.018 mmol) as a TFA salt. APCI: [M+H]+ m/z 450.1. 1H NMR (500 MHz, DMSO-d6): δ 10.34 (1H, s), 8.86 (1H, d, J=4.89 Hz), 8.43 (2H, broad s), 8.14 (1H, s), 8.01 (1H, s), 7.67 (1H, d, J=8.10 Hz), 7.39 (1H, t, 7.88 Hz), 7.34-7.29 (2H, m), 3.18-3.02 (2H, m), 2.61-2.54 (2H, m), 1.92-1.77 (2H, m), 1.51 (3H, s), 1.55-1.41 (1H, m), 1.38-1.22 (1H, m). rhSYK activity=+++

後処理

  1. customThe solvent was removed by evaporation
  2. concentrationThe residue was concentrated
  3. customdried under high-vacuum

出典と根拠

ORDレコード
ord-c077f76af17a435198ecb18342350499
出典データセット
uspto-grants-2014_06
特許番号
US08759366B2

反応ノート

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