(2S)-N-methylpyrrolidine-2-carboxamide → (s)-1-[2-(4-{2-[2-(4-Chloro-benzoylamino)-thiazol-4-yl]-acetyl}-piperazin-1-yl)-acetyl]-pyrrolidine-2-carboxylic acid methylamide

HRID 2237539Notes

Reaction equation

HRID 2237539 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][C:15]([N:17]3[CH2:22][CH2:21][N:20]([CH2:23][C:24]([OH:26])=O)[CH2:19][CH2:18]3)=[O:16])[N:13]=2)=[O:7])=[CH:4][CH:3]=1.[NH:29]1[CH2:37][CH2:36][CH2:35][C@H:30]1[C:31]([NH:33][CH3:34])=[O:32]>>[CH3:34][NH:33][C:31]([C@@H:30]1[CH2:35][CH2:36][CH2:37][N:29]1[C:24](=[O:26])[CH2:23][N:20]1[CH2:21][CH2:22][N:17]([C:15](=[O:16])[CH2:14][C:12]2[N:13]=[C:9]([NH:8][C:6](=[O:7])[C:5]3[CH:27]=[CH:28][C:2]([Cl:1])=[CH:3][CH:4]=3)[S:10][CH:11]=2)[CH2:18][CH2:19]1)=[O:32]

Participants

3

Reactant 2

HCID 10374482(2S)-N-methylpyrrolidine-2-carboxamideHCID 59698876(4-{2-[2-(4-Chloro-benzoylamino)-thiazol-4-yl]-acetyl}-piperazin-1-yl)-acetic acid

Product 1

HCID 59698875(s)-1-[2-(4-{2-[2-(4-Chloro-benzoylamino)-thiazol-4-yl]-acetyl}-piperazin-1-yl)-acetyl]-pyrrolidine-2-carboxylic acid methylamide

Procedure

In analogy to example 22.3, (4-{2-[2-(4-chloro-benzoylamino)-thiazol-4-yl]-acetyl}-piperazin-1-yl)-acetic acid (example 22.2) was coupled with H-Pro-NHMe, using general method C, to give (S)-1-[2-(4-{2-[2-(4-chloro-benzoylamino)-thiazol-4-yl]-acetyl}-piperazin-1-yl)-acetyl]-pyrrolidine-2-carboxylic acid methylamide. White solid. MS 533.3 ([M+H]+)

Sources & evidence

ORD record
ord-d0b14e82a267478d8f5db06c10d997c9
Source dataset
uspto-grants-2010_05
Patent number
US07718659B2

Reaction notes

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