(R)-3-Pyrrolidinol → 3-[3-(3-Chloro-5-fluorophenyl)-5-{[(3R)-3-hydroxypyrrolidin-1-yl]carbonyl}furan-2-yl]benzenecarbonitrile

HRID 2190139Notes

Reaction equation

HRID 2190139 reaction equation
ClC1C=C(C2C=[C:10]([C:20]([N:22]3[CH2:27][CH2:26]NC(=O)C3)=O)[O:11]C=2C2C=CC(F)=CC=2)C=CC=1.[Cl:29][C:30]1[CH:31]=[C:32]([C:37]2[CH:38]=[C:39]([C:50](O)=[O:51])[O:40][C:41]=2[C:42]2[CH:47]=[CH:46][CH:45]=[C:44]([C:48]#[N:49])[CH:43]=2)[CH:33]=[C:34]([F:36])[CH:35]=1.N1CC[C@@H](O)C1>>[Cl:29][C:30]1[CH:31]=[C:32]([C:37]2[CH:38]=[C:39]([C:50]([N:22]3[CH2:27][CH2:26][C@@H:10]([OH:11])[CH2:20]3)=[O:51])[O:40][C:41]=2[C:42]2[CH:43]=[C:44]([C:48]#[N:49])[CH:45]=[CH:46][CH:47]=2)[CH:33]=[C:34]([F:36])[CH:35]=1

Participants

4

Reactant 3

HCID 2759337(R)-3-PyrrolidinolHCID 580647984-(3-Chloro-5-fluorophenyl)-5-(3-cyanophenyl)furan-2-carboxylic acidHCID 580648004-{[4-(3-Chlorophenyl)-5-(4-fluorophenyl)furan-2-yl]carbonyl}piperazin-2-one

Product 1

HCID 468328783-[3-(3-Chloro-5-fluorophenyl)-5-{[(3R)-3-hydroxypyrrolidin-1-yl]carbonyl}furan-2-yl]benzenecarbonitrile

Procedure

The preparation of the title compound takes place in analogy to the synthesis of the compound from Example 6 starting with the compound from Example 20A. 1.1 equivalents of (3R)-pyrrolidin-3-ol are used. 51.0 mg (85% of theory) of the title compound are obtained.

Sources & evidence

ORD record
ord-4215eaa9ba2147d499946e84d12cd0f6
Source dataset
uspto-grants-2012_12
Patent number
US08324268B2

Reaction notes

Loading…