Acetonitrile → benzamide, 2-amino-N-[2-[[(3R)-1-[(4-ethenylphenyl)methyl]-3-pyrrolidinyl]amino]-2-oxoethyl]-5-(trifluoromethyl)-

HRID 2187776Notes

Reaction equation

[NH2:1][C:2]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][C:8]([NH:10][C@@H:11]1[CH2:15][CH2:14][NH:13][CH2:12]1)=[O:9])=[O:5].[CH:24]([C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Cl)=[CH:28][CH:27]=1)=[CH2:25].C(#N)C>C(Cl)(Cl)Cl>[NH2:1][C:2]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][C:8]([NH:10][C@@H:11]1[CH2:15][CH2:14][N:13]([CH2:30][C:29]2[CH:32]=[CH:33][C:26]([CH:24]=[CH2:25])=[CH:27][CH:28]=2)[CH2:12]1)=[O:9])=[O:5]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of (R)-3-[{N-(2-amino-5-(trifluoromethyl)benzoyl)glycyl}amino]pyrrolidine (0.05 mmol), 4-vinylbenzyl chloride (9.9 mg, 0.065 mmol), piperidinomethylpolystyrene (60 mg), acetonitrile (1.0 mL) and chloroform (0.30 mL) was stirred at 50° C. for 12 h. The reaction mixture was cooled, loaded onto Varian™ SCX column and washed with CH3OH (15 mL). Product was eluted using 2 N NH3 in CH3OH (5 mL) and concentrated to afford (R)-3-[{N-(2-amino-5-(trifluoromethyl)benzoyl)glycyl}amino]-1-(4-vinylbenzyl)pyrrolidine (Compound No. 1701) (19.6 mg, 88%): The purity was determined by RPLC/MS (92%); ESI/MS m/e 547.2 (M++H, C23H25ClF3N4O2).

Workup

temperatureThe reaction mixture was cooled
washwashed with CH3OH (15 mL)
washProduct was eluted
concentrationconcentrated

Sources & evidence

ORD record: ord-a38dbf8c0d2846c1805c44fff500f336
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06410566B1

Reaction notes

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