HCID 18187555, compound → HCID 20664097, compound

HRID 1068246Notes

Reaction equation

HRID 1068246 reaction equation
[CH:1]([C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)[CH2:6][N:5]([C@@H:15]([CH:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[C:16]([O:18]CC2C=CC(OC)=CC=2)=[O:17])[CH2:4]1)=O.[CH2:33]([C:40]1[S:41][C:42]([CH:47]2[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]2)=[C:43]([CH2:45][CH3:46])[N:44]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[CH2:33]([C:40]1[S:41][C:42]([CH:47]2[CH2:52][CH2:51][N:50]([CH2:1][C@@H:3]3[C@@H:7]([C:8]4[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=4)[CH2:6][N:5]([C@@H:15]([CH:28]([CH2:29][CH3:30])[CH2:31][CH3:32])[C:16]([OH:18])=[O:17])[CH2:4]3)[CH2:49][CH2:48]2)=[C:43]([CH2:45][CH3:46])[N:44]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

3

Reactant 2

HCID 18187555HCID 18187555, compoundHCID 57066216HCID 57066216, compound

Product 1

HCID 20664097HCID 20664097, compoundYield 26.3%

Procedure

Reductive amination of 20 mg (0.045 mmol) of 2(S)-(3-(R)-formyl-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-3-ethylvaleric acid, 4-methoxybenzyl ester with 15 mg (0.42 mmol) of 4-(2-benzyl-4-ethyl-thiazol-5-yl)piperidine as described in example 527 step D, and removal of 4-methoxybenzyl ester according to example 527 step E furnished 7 mg of the title compound. Mass spec. 592.4 (M+1), HPLC A 2.36 min.

Sources & evidence

ORD record
ord-b88cd7d4840f40d6b237f641d30e8f42
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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