Cyclopropanecarbonyl chloride → HCID 89814970, compound

HRID 717088Notes

Reaction equation

HRID 717088 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[CH3:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[C:11]([C:19]1[CH:20]=[N:21][C:22]([N:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[N:23][CH:24]=1)[NH:12][C:13]2=[O:18].C(N(CC)C(C)C)(C)C>C(Cl)Cl>[CH:1]1([C:4]([N:28]2[CH2:27][CH2:26][N:25]([C:22]3[N:23]=[CH:24][C:19]([C:11]4[NH:12][C:13](=[O:18])[C:14]5[C:9]([CH:10]=4)=[C:8]([CH3:7])[CH:17]=[CH:16][CH:15]=5)=[CH:20][N:21]=3)[CH2:30][CH2:29]2)=[O:5])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 71736113HCID 71736113, compound

Product 1

HCID 89814970HCID 89814970, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyclopropylcarbonyl chloride (9 μL, 2.28 mmol) was added to a stirred solution of 5-methyl-3-(2-piperazin-1-yl-pyrimidin-5-yl)-2H-isoquinolin-1-one (36 mg, 0.11 mmol) and N,N-diisopropylethylamine (23 μL, 0.132 mmol) in CH2Cl2 (2 mL) at −20° C. and allowed to stir for 10 min. The reaction mixture was concentrated in vacuo. The crude residue was purified by reverse phase preparative HPLC-MS to afford 3-[2-(4-cyclopropanecarbonyl-piperazin-1-yl)-pyrimidin-5-yl]-5-methyl-2H-isoquinolin-1-one as a white solid (19 mg, 45%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe crude residue was purified by reverse phase preparative HPLC-MS

Sources & evidence

ORD record
ord-fa29ccf2e899483d98002e6fdfb6d789
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

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