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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
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HRID 592216 반응식
[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]
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참가 물질

4

반응물 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

생성물 1

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

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-62d97e58a04044f0a5290c7fe759102b
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09238646B2

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