Cyclopropanecarbonyl chloride → HCID 52920086, compound

HRID 1615386Notes

Reaction equation

HRID 1615386 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]4[CH:18]=[C:19]([NH:23][C:24]([NH:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[O:33][CH3:34])=[O:25])[CH:20]=[CH:21][CH:22]=4)[CH:15]=3)[CH:10]=[CH:9]2)[CH:3]=1.[CH:35]1([C:38](Cl)=[O:39])[CH2:37][CH2:36]1>N1C=CC=CC=1>[CH3:34][O:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[NH:26][C:24](=[O:25])[NH:23][C:19]1[CH:18]=[C:17]([C:14]2[CH:15]=[C:16]3[C:11]([CH:10]=[CH:9][N:8]3[C:4]3[N:5]=[CH:6][N:7]=[C:2]([NH:1][C:38]([CH:35]4[CH2:37][CH2:36]4)=[O:39])[CH:3]=3)=[CH:12][CH:13]=2)[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 52919483HCID 52919483, compound

Product 1

HCID 52920086HCID 52920086, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

Pyridine was added to 1-(3-(1-(6-aminopyrimidin-4-yl)-1H-indol-6-yl)phenyl)-3-(2-methoxyphenyl)urea (13 mg, 0.029 mmol). At room temperature, cyclopropylcarbonyl chloride (17 μL, 0.29 mmol) was added. The reaction solution was stirred at 50° C. for 1.5 hours. After cooling to room temperature, the reaction solution was concentrated under reduced pressure. Purification of the residue by column chromatography (silica gel; EA:Hx=1:4→DCM:MeOH=20:1) yielded N-(6-(6-(3-(3-(2-methoxyphenyl)ureido)phenyl)-1H-indol-1-yl)pyrimidin-4-yl)cyclopropanecarboxamide as white solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. customPurification of the residue by column chromatography (silica gel; EA:Hx=1:4→DCM:MeOH=20:1)

Sources & evidence

ORD record
ord-dd2be409faf34543a58b02c64146b052
Source dataset
uspto-grants-2014_07
Patent number
US08765749B2

Reaction notes

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