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

HRID 40683

반응식

HRID 40683 반응식
[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]

참가 물질

5

반응물 3

HCID 6367Acetyl chloride2회HCID 81531DiisopropylethylamineHCID 442045585-(8-Aminoisoquinolin-3-ylamino)pyrazine-2-carbonitrile

생성물 1

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

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ac3b96b0049f4acba0cc8a0b36463c4e
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530468B2

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