Water → (2-{4-[1-(2-Fluoro-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidin-1-yl}-5-methyl-pyrimidin-4-yl)-dimethyl-amine

HRID 1958418ノート

反応式

HRID 1958418 の反応式
Cl.[F:2][C:3]1[CH:8]=[C:7]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:6]=[CH:5][C:4]=1[N:13]1[C:17]2=[N:18][CH:19]=[N:20][C:21]([O:22][CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[C:16]2[CH:15]=[N:14]1.Cl[C:30]1[N:35]=[C:34]([N:36]([CH3:38])[CH3:37])[CH:33]=[C:32](C)[N:31]=1.[C:40]([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[F:2][C:3]1[CH:8]=[C:7]([S:9]([CH3:12])(=[O:10])=[O:11])[CH:6]=[CH:5][C:4]=1[N:13]1[C:17]2=[N:18][CH:19]=[N:20][C:21]([O:22][CH:23]3[CH2:24][CH2:25][N:26]([C:30]4[N:35]=[C:34]([N:36]([CH3:38])[CH3:37])[C:33]([CH3:40])=[CH:32][N:31]=4)[CH2:27][CH2:28]3)=[C:16]2[CH:15]=[N:14]1

参加物

6

反応物 4

HCID 962WaterHCID 10813CrimidineHCID 11430Potassium CarbonateHCID 218977401-(2-Fluoro-4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine hydrochloride

生成物 1

HCID 21897401(2-{4-[1-(2-Fluoro-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidin-1-yl}-5-methyl-pyrimidin-4-yl)-dimethyl-amine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
65 °C

実験手順

1-(2-Fluoro-4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine HCl salt (0.3 g, 0.97 mmol) and (2-chloro-6-methyl-pyrimidin-4-yl)-dimethyl-amine (285 mg, 0.97 mmol) were dissolved in DMF (10 mL). The solution was treated with K2CO3 (398 mg, 2.91 mmol) at an ambient temperature. After stirring at 65° C. for five hours, the reaction was poured into H2O (20 mL). The organic compound was extracted with ethyl acetate (30 mL) and washed with brine. The ethyl acetate layer was dried over MgSO4 and concentrated under vacuum. The residue was purified over SiO2 to afford Compound A212 (312 mg, 65.2%). 1H NMR (400 Mz, DMSO-d6) δ 8.69 (s, 1H), 8.64 (s, 1H), 8.17 (dd, J=8.4, 1.8, 1H), 8.08 (d, J=4.2, 1H), 8.01 (dd, J=8.4, 1.8, 1H), 7.72 (s, 1H), 5.65 (m, 1H), 4.23˜4.20 (m, 2H), 3.50˜3.46 (m, 2H), 3.39 (s, 3H), 3.00 (s, 6H), 2.13 (s, 3H), 2.10˜2.09 (m, 2H), 1.77˜1.72 (m, 2H). LCMS 527.5 [M+1].

後処理

  1. extractionThe organic compound was extracted with ethyl acetate (30 mL)
  2. washwashed with brine
  3. dry with materialThe ethyl acetate layer was dried over MgSO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified over SiO2
  6. customto afford Compound A212 (312 mg, 65.2%)

出典と根拠

ORDレコード
ord-906c0185a09147e181caf74a777cdafa
出典データセット
uspto-grants-2013_04
特許番号
US08410119B2

反応ノート

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