Trifluoroacetic acid → 4-(4-methanesulfonyl-phenoxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine trifluoroacetate salt

HRID 1931600

反応式

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C(OC([N:15]1[CH2:20][CH2:19][CH:18]([N:21]2[C:25]3=[N:26][CH:27]=[N:28][C:29]([O:30][C:31]4[CH:36]=[CH:35][C:34]([S:37]([CH3:40])(=[O:39])=[O:38])=[CH:33][CH:32]=4)=[C:24]3[CH:23]=[N:22]2)[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:40][S:37]([C:34]1[CH:33]=[CH:32][C:31]([O:30][C:29]2[N:28]=[CH:27][N:26]=[C:25]3[N:21]([CH:18]4[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]4)[N:22]=[CH:23][C:24]=23)=[CH:36][CH:35]=1)(=[O:39])=[O:38]

参加物

実験手順

Trifluoroacetic acid (38.0 mL, 512 mmol) was added to a cooled solution of 4-[4-(4-methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (Example 59; 12.0 g, 25.4 mmol) in dichloromethane (70 mL) at about 0° C. The reaction mixture was stirred for 3 h. The solvent was evaporated under reduced pressure, and the residue was coevaporated three times with toluene to give 4-(4-methanesulfonyl-phenoxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine trifluoroacetate salt (12.0 g, 97%) as an off-white solid which was used in the next step without further purification. 1H NMR (300 MHz, DMSO-d6) δ 2.14-2.17 (m, 2H), 2.32-2.41 (m, 2H), 3.22-3.30 (m, 2H), 3.30 (methyl sulfonyl peak and water peak), 3.45-3.50 (m, 2H), 5.15-5.21 (m, 1H), 7.62-7.64 (m, 2H), 8.06-8.08 (m, 2H), 8.44 (s, 1H), 8.50-8.58 (br s, 1H), 8.59 (s, 1H), 8.76-8.83 (br s, 1H). Mass spectrum (ES) MH+=374.

後処理

customThe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード: ord-6983abdeac9144e3ab1ec033ac091c72
出典データセット: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08188098B2

反応式

参加物

反応物 2

生成物 1

試薬・触媒・溶媒 1

実験手順

後処理

出典と根拠

関連ノート