1-(2-Ethoxy-benzoyl)-3-iodomethyl-pyrrolidine-3-carboxylic acid ethyl ester → 3-[5-(4-Chloro-phenyl)-pyrazin-2-yloxymethyl]-1-(2-ethoxy-benzoyl)-pyrrolidine-3-carboxylic acid ethyl ester

HRID 2060287Notes

Reaction equation

HRID 2060287 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][C:11]([OH:14])=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[CH2:15]([O:17][C:18]([C:20]1([CH2:36]I)[CH2:24][CH2:23][N:22]([C:25](=[O:35])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[O:32][CH2:33][CH3:34])[CH2:21]1)=[O:19])[CH3:16]>>[CH2:15]([O:17][C:18]([C:20]1([CH2:36][O:14][C:11]2[CH:10]=[N:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[CH:13][N:12]=2)[CH2:24][CH2:23][N:22]([C:25](=[O:35])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[O:32][CH2:33][CH3:34])[CH2:21]1)=[O:19])[CH3:16]

Participants

3

Reactant 2

HCID 593222281-(2-Ethoxy-benzoyl)-3-iodomethyl-pyrrolidine-3-carboxylic acid ethyl esterHCID 178516753HCID 178516753, compound

Product 1

HCID 593222043-[5-(4-Chloro-phenyl)-pyrazin-2-yloxymethyl]-1-(2-ethoxy-benzoyl)-pyrrolidine-3-carboxylic acid ethyl ester

Procedure

The title compound was prepared according to the method described for Preparation 29 using 5-(4-chloro-phenyl)-pyrazin-2-ol (Preparation 25) and 1-(2-ethoxy-benzoyl)-3-iodomethyl-pyrrolidine-3-carboxylic acid ethyl ester (Preparation 16) to afford the racemate as a white solid (86 mg, 30%)

Sources & evidence

ORD record
ord-7c06bcc80f374955a99229bd9a7300ea
Source dataset
uspto-grants-2012_10
Patent number
US08278343B2

Reaction notes

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