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Potassium Phosphate, Tribasic → N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(4-(2-methylpyrimidin-4-yl)-3-(trifluoromethyl)phenyl)acetamide

HRID 592216
ノート
印刷プレビュー

反応式

HRID 592216 の反応式
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:38])[CH2:18][C:19]3[CH:24]=[CH:23][C:22](B4OC(C)(C)C(C)(C)O4)=[C:21]([C:34]([F:37])([F:36])[F:35])[CH:20]=3)=[N:14][CH:15]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].Cl[C:40]1[CH:45]=[CH:44][N:43]=[C:42]([CH3:46])[N:41]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>>[C:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:38])[CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:40]4[CH:45]=[CH:44][N:43]=[C:42]([CH3:46])[N:41]=4)=[C:21]([C:34]([F:36])([F:35])[F:37])[CH:20]=3)=[N:14][CH:15]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 4244474-Chloro-2-methylpyrimidineHCID 58447853N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)phenyl)acetamide

生成物 1

HCID 58447882N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(4-(2-methylpyrimidin-4-yl)-3-(trifluoromethyl)phenyl)acetamide

反応条件

温度
100 °C

実験手順

A mixture of N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)phenyl)acetamide 192-3 (53 mg, 0.1 mmol), 4-chloro-2-methylpyrimidine 192-4 (18 mg, 0.14 mmol) Pd(PPh3)4 (11 mg, 0.01 mmol) and K3PO4 (42 mg, 0.2 mmol) in dioaxane (1.0 mL) was flushed with nitrogen and heated to 100° C. for 2 hours. The salt was removed by filtration and the filtrate was taken to dryness by rotary evaporation. The residue was purified by reverse phase HPLC to give N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(4-(2-methylpyrimidin-4-yl)-3-(trifluoromethyl)phenyl)acetamide 192. MS m/z 499.2 (M+1). 1H NMR 400 MHz (DMSO-d6) δ0.58 (s, 1H), 8.77 (d, 1H), 8.02 (s, 1H), 7.89 (m, 2H), 7.73 (d, 1H), 7.54 (d, 1H), 7.42 (m, 2H), 3.76 (s, 2H), 3.66 (b, 4H), 3.14 (b, 2H), 3.07 (b, 2H), 2.64 (s, 3H), 2.03 (s, 3H).

後処理

  1. customwas flushed with nitrogen
  2. customThe salt was removed by filtration
  3. customthe filtrate was taken to dryness by rotary evaporation
  4. customThe residue was purified by reverse phase HPLC

出典と根拠

ORDレコード
ord-62d97e58a04044f0a5290c7fe759102b
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09238646B2

反応ノート

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