Acetic Acid → 4-((4-((3S)-3-cyano-3-isopropyl-2-oxopyrrolidin-1-yl) pyrimidin-2-yl)amino)-N-methylbenzamide hydrochloride

HRID 714794Notes

Reaction equation

HRID 714794 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:12][CH2:11][C@:10]([CH:15]([CH3:17])[CH3:16])([C:13]#[N:14])[C:9]2=[O:18])[CH:5]=[CH:4][N:3]=1.[NH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([NH:26][CH3:27])=[O:25])=[CH:22][CH:21]=1.C(O)(=O)C>C(O)C>[ClH:1].[C:13]([C@@:10]1([CH:15]([CH3:17])[CH3:16])[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:24]([NH:26][CH3:27])=[O:25])=[CH:28][CH:29]=3)[N:7]=2)[C:9]1=[O:18])#[N:14]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2355164-Amino-N-methylbenzamideHCID 117840068(3S)-1-(2-chloropyrimidin-4-yl)-3-isopropyl-2-oxopyrrolidine-3-carbonitrile

Product 1

HCID 1178406794-((4-((3S)-3-cyano-3-isopropyl-2-oxopyrrolidin-1-yl) pyrimidin-2-yl)amino)-N-methylbenzamide hydrochlorideYield 75.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (3S)-1-(2-chloropyrimidin-4-yl)-3-isopropyl-2-oxopyrrolidine-3-carbonitrile (55 mg) obtained in Step A, 4-amino-N-methylbenzamide (37 mg) and acetic acid (13 μL) in ethanol (2 mL) was stirred in a microwave reactor at 150° C. for 1 hr, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate). To a solution of the residue (87 mg) in ethanol (3 mL) was added 1M hydrochloric acid (230 μL), and the solvent was evaporated under reduced pressure. The residue was recrystallized (diisopropyl ether/ethanol) to give the title compound (65 mg).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe obtained residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)
  3. additionTo a solution of the residue (87 mg) in ethanol (3 mL) was added 1M hydrochloric acid (230 μL)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was recrystallized (diisopropyl ether/ethanol)

Sources & evidence

ORD record
ord-001b6de79426471f9347ff939e9a0b5c
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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