Cyclopropanecarbonyl chloride → methyl 2-(2-{(cyclopropylcarbonyl)[3-(1H-pyrazol-1-yl)phenyl]amino}ethyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

HRID 1616174Notes

Reaction equation

HRID 1616174 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[CH:5]=[CH:4][N:3]1[CH2:16][CH2:17][NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([N:25]2[CH:29]=[CH:28][CH:27]=[N:26]2)[CH:20]=1.C(N(CC)C(C)C)(C)C.[CH:39]1([C:42](Cl)=[O:43])[CH2:41][CH2:40]1>C(Cl)Cl>[CH:39]1([C:42]([N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N:25]3[CH:29]=[CH:28][CH:27]=[N:26]3)[CH:20]=2)[CH2:17][CH2:16][N:3]2[CH:4]=[CH:5][C:6]3[C:11](=[CH:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=3)[C:2]2=[O:1])=[O:43])[CH2:41][CH2:40]1

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 67283555methyl 1-oxo-2-(2-{[3-(1H-pyrazol-1-yl)phenyl]amino}ethyl)-1,2-dihydroisoquinoline-7-carboxylate

Product 1

HCID 67282584methyl 2-(2-{(cyclopropylcarbonyl)[3-(1H-pyrazol-1-yl)phenyl]amino}ethyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 1-oxo-2-(2-{[3-(1H-pyrazol-1-yl)phenyl]amino}ethyl)-1,2-dihydroisoquinoline-7-carboxylate (77 mg, 0.20 mmol) dissolved in methylene chloride (1.5 mL) was added N,N-diisopropylethylamine (69 μL, 0.4 mmol) and cyclopropanecarbonyl chloride (27 μL, 0.30 mmol). The reaction mixture was stirred at rt for 1 h. The mixture was then concentrated to dryness and the residue was purified by flash silica gel chromatography (30% to 100% EtOAc/hexanes) to afford methyl 2-(2-{(cyclopropylcarbonyl)[3-(1H-pyrazol-1-yl)phenyl]amino}ethyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (77 mg, 85%). LC-MS: (FA) ES+ 457.

Workup

  1. concentrationThe mixture was then concentrated to dryness
  2. customthe residue was purified by flash silica gel chromatography (30% to 100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-94143c91c46a44ba952a5deac50e7bc1
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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