3-Iodomethyl-1-(2-methoxy-benzoyl)-pyrrolidine-3-carboxylic acid ethyl ester → 3-[4-(5-Cyano-pyrimidin-2-yl)-phenoxymethyl]-1-(2-methoxy-benzoyl)-pyrrolidine-3-carboxylic acid ethyl ester

HRID 2060272Notes

Reaction equation

HRID 2060272 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[CH2:16]([O:18][C:19]([C:21]1([CH2:36]I)[CH2:25][CH2:24][N:23]([C:26](=[O:35])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH3:34])[CH2:22]1)=[O:20])[CH3:17]>>[CH2:16]([O:18][C:19]([C:21]1([CH2:36][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[N:9]=[CH:10][C:11]([C:14]#[N:15])=[CH:12][N:13]=3)=[CH:6][CH:7]=2)[CH2:25][CH2:24][N:23]([C:26](=[O:35])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH3:34])[CH2:22]1)=[O:20])[CH3:17]

Participants

3

Reactant 2

HCID 593221723-Iodomethyl-1-(2-methoxy-benzoyl)-pyrrolidine-3-carboxylic acid ethyl esterHCID 1356751332-(4-Hydroxyphenyl)pyrimidine-5-carbonitrile

Product 1

HCID 593222313-[4-(5-Cyano-pyrimidin-2-yl)-phenoxymethyl]-1-(2-methoxy-benzoyl)-pyrrolidine-3-carboxylic acid ethyl ester

Procedure

The title compound was prepared according to the method described for Preparation 29 using 2-(4-hydroxy-phenyl)-pyrimidine-5-carbonitrile and 3-iodomethyl-1-(2-methoxy-benzoyl)-pyrrolidine-3-carboxylic acid ethyl ester (Preparation 15) to afford the racemate as a white solid (53 mg, 30%)

Sources & evidence

ORD record
ord-f8415d9aa418491194bd71f448e29955
Source dataset
uspto-grants-2012_10
Patent number
US08278343B2

Reaction notes

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