Acetyl chloride → N-(3-(5-cyanopyrazin-2-ylamino)isoquinolin-8-yl)acetamide

HRID 40683

反応式

HRID 40683 の反応式
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[CH:14]=[N:13][C:12]([NH:16][C:17]1[N:18]=[CH:19][C:20]([C:23]#[N:24])=[N:21][CH:22]=1)=[CH:11]2.C(N(C(C)C)CC)(C)C>ClCCCl>[C:23]([C:20]1[N:21]=[CH:22][C:17]([NH:16][C:12]2[N:13]=[CH:14][C:15]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[CH:7][C:6]=3[NH:5][C:1](=[O:3])[CH3:2])=[N:18][CH:19]=1)#[N:24]

参加物

5

反応物 3

HCID 6367Acetyl chloride2 回HCID 81531DiisopropylethylamineHCID 442045585-(8-Aminoisoquinolin-3-ylamino)pyrazine-2-carbonitrile

生成物 1

HCID 44204559N-(3-(5-cyanopyrazin-2-ylamino)isoquinolin-8-yl)acetamide収率 32%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

Acetyl chloride (13 mg, 0.16 mmol) was added to a solution of 5-(8-aminoisoquinolin-3-ylamino)pyrazine-2-carbonitrile (36 mg, 0.14 mmol) and diisopropylethylamine (39 mg, 0.30 mmol) in DCE (1.5 mL). The reaction mixture stirred at room temperature for 16 hours and another portion of acetyl chloride (6.5 mg, 0.08 mmol) was added. Stirring was continued for a further 24 hours. The reaction mixture was washed once with water and the organic phase was dried (Na2SO4) and concentrated to dryness. Preparative HPLC gave N-(3-(5-cyanopyrazin-2-ylamino)isoquinolin-8-yl)acetamide (13.4 mg, 0.044 mmol, 32%). 1H NMR (d6-DMSO, 400 MHz) δ 11.05 (br s, 1H), 10.20 (s, 1H), 9.36 (s, 1H), 8.82 (d, 1H, J=1.2 Hz), 8.72 (d, 1H, J=1.2 Hz), 8.48 (s, 1H), 7.65-7.75 (m, 3H), 2.22 (s, 3H). LC-MS (2) Rt=1.96 min; m/z (ESI+) 305 (M+H).

後処理

  1. stirringStirring
  2. waitwas continued for a further 24 hours
  3. washThe reaction mixture was washed once with water
  4. dry with materialthe organic phase was dried (Na2SO4)
  5. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-ac3b96b0049f4acba0cc8a0b36463c4e
出典データセット
uspto-grants-2013_09
特許番号
US08530468B2

関連ノート

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