tert-butyl N-(pyrrolidin-3-yl)carbamate → {1-[2-(4-{2-[2-(4-Chloro-benzoylamino)-thiazol-4-yl]-acetyl}-piperazin-1-yl)-acetyl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester

HRID 901016Notes

Reaction equation

HRID 901016 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](O)=[O:25])[CH2:19][CH2:18]3)=[O:16])[N:13]=2)=[O:7])=[CH:4][CH:3]=1.[C:29]([O:33][C:34]([NH:36][CH:37]1[CH2:41][CH2:40][NH:39][CH2:38]1)=[O:35])([CH3:32])([CH3:31])[CH3:30]>>[C:29]([O:33][C:34](=[O:35])[NH:36][CH:37]1[CH2:41][CH2:40][N:39]([C:24](=[O:25])[CH2:23][N:20]2[CH2:21][CH2:22][N:17]([C:15](=[O:16])[CH2:14][C:12]3[N:13]=[C:9]([NH:8][C:6](=[O:7])[C:5]4[CH:27]=[CH:28][C:2]([Cl:1])=[CH:3][CH:4]=4)[S:10][CH:11]=3)[CH2:18][CH2:19]2)[CH2:38]1)([CH3:32])([CH3:30])[CH3:31]

Participants

3

Reactant 2

HCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 59698876(4-{2-[2-(4-Chloro-benzoylamino)-thiazol-4-yl]-acetyl}-piperazin-1-yl)-acetic acid

Product 1

HCID 59698888{1-[2-(4-{2-[2-(4-Chloro-benzoylamino)-thiazol-4-yl]-acetyl}-piperazin-1-yl)-acetyl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester

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 3-(tert-butyloxycarbonylamino)pyrrolidine, using general method C, to give {1-[2-(4-{2-[2-(4-chloro-benzoylamino)-thiazol-4-yl]-acetyl}-piperazin-1-yl)-acetyl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester. Off-white solid. MS 591.3 ([M+H]+)

Sources & evidence

ORD record
ord-ad4cd707f30b4ac88041529544ec7c2c
Source dataset
uspto-grants-2008_04
Patent number
US07361672B2

Reaction notes

Loading…