Acetic Acid → 1-(4-((4-((3S)-3-cyano-3-cyclopropyl-2-oxopyrrolidin-1-yl)pyrimidin-2-yl)amino)phenyl)cyclopropanecarboxylic acid hydrochloride

HRID 714859Notes

Reaction equation

HRID 714859 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:12][CH2:11][C@:10]([CH:15]3[CH2:17][CH2:16]3)([C:13]#[N:14])[C:9]2=[O:18])[CH:5]=[CH:4][N:3]=1.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2([C:29]([OH:31])=[O:30])[CH2:28][CH2:27]2)=[CH:22][CH:21]=1.C(O)(=O)C>CC(O)C>[ClH:1].[C:13]([C@@:10]1([CH:15]2[CH2:17][CH2:16]2)[CH2:11][CH2:12][N:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:19][C:20]3[CH:21]=[CH:22][C:23]([C:26]4([C:29]([OH:31])=[O:30])[CH2:28][CH2:27]4)=[CH:24][CH:25]=3)[N:7]=2)[C:9]1=[O:18])#[N:14]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 666623781-(4-Aminophenyl)cyclopropanecarboxylic acidHCID 117840203(3S)-1-(2-chloropyrimidin-4-yl)-3-cyclopropyl-2-oxopyrrolidine-3-carbonitrile

Product 1

HCID 1178407711-(4-((4-((3S)-3-cyano-3-cyclopropyl-2-oxopyrrolidin-1-yl)pyrimidin-2-yl)amino)phenyl)cyclopropanecarboxylic acid hydrochlorideYield 78.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of (3S)-1-(2-chloropyrimidin-4-yl)-3-cyclopropyl-2-oxopyrrolidine-3-carbonitrile (100 mg) obtained in Step E of Example 103, 1-(4-aminophenyl)cyclopropanecarboxylic acid (67 mg) obtained in Step C of Example 145 and acetic acid (30 μL) in 2-propanol (1.5 mL) was stirred in a microwave reactor at 150° C. for 1 hr, and the resulting solid was collected by filtration to give the title compound (130 mg).

Workup

  1. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-5fdcf33b1c8f4f47be2658e3becf6fff
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

Loading…