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

HRID 40683

Reaction equation

HRID 40683 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-ac3b96b0049f4acba0cc8a0b36463c4e
Source dataset
uspto-grants-2013_09
Patent number
US08530468B2

Linked notes

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