Iodoethane → HCID 66847249、化合物

HRID 1466585ノート

反応式

HRID 1466585 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:26])=[C:6]([C:8]2[C:12]([NH:13][C:14]([C:16]3[CH:17]=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[N:21][C:20]=34)=[O:15])=[CH:11][N:10]([CH3:25])[N:9]=2)[CH:7]=1.I[CH2:28][CH3:29].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][CH2:28][CH3:29])=[C:6]([C:8]2[C:12]([NH:13][C:14]([C:16]3[CH:17]=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[N:21][C:20]=34)=[O:15])=[CH:11][N:10]([CH3:25])[N:9]=2)[CH:7]=1

参加物

5

反応物 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 136041870HCID 136041870、化合物

生成物 1

HCID 66847249HCID 66847249、化合物収率 54%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
45 °C

実験手順

To a solution of N-(3-(5-chloro-2-hydroxyphenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (61.1 mg, 0.166 mmol) in 3.0 mL acetone was added iodoethane (26.0 μL, 0.325 mmol) and potassium carbonate (70.6 mg, 0.511 mmol) The reaction was stirred at 45° C. for 3 hours. The reaction mixture was partitioned between ethyl acetate and water, and the organic portion washed with brine, dried over magnesium sulfate, and concentrated. The crude product was purified by reverse phase HPLC and lyophilized to give 34.8 mg (54%) N-(3-(5-chloro-2-ethoxyphenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide. LCMS (ESI) m+H=397.1; 1H NMR (400 MHz, DMSO-d6) δ: 9.68 (s, 1H), 9.33 (dd, J=7.0, 1.6, 1H), 8.73 (dd, J=4.2, 1.6, 1H), 8.66 (s, 1H), 8.28 (s, 1H), 7.46 (dd, J=8.8, 2.7, 1H), 7.38 (d, J=2.7, 1H), 7.32-7.23 (m, 2H), 4.12 (q, J=6.9, 2H), 3.91 (s, 3H), 1.04 (t, J=6.9, 3H).

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washthe organic portion washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by reverse phase HPLC

出典と根拠

ORDレコード
ord-ea5a968d473a4529a098305720f5adea
出典データセット
uspto-grants-2015_04
特許番号
US08999998B2

反応ノート

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