(3S)-(+)-1-Benzyl-3-aminopyrrolidine → (2S)-N2-[(3S)-1-benzylpyrrolidin-3-yl]-1-(6-chloro-1,3-benzothiazol-2-yl)-2-piperidinecarboxamide

HRID 841934Notes

Reaction equation

HRID 841934 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]=[C:7]([N:9]3[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]3[C:15]([OH:17])=O)[S:8][C:4]=2[CH:3]=1.[CH2:20]([N:27]1[CH2:31][CH2:30][C@H:29]([NH2:32])[CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH2:20]([N:27]1[CH2:31][CH2:30][C@H:29]([NH:32][C:15]([C@@H:10]2[CH2:11][CH2:12][CH2:13][CH2:14][N:9]2[C:7]2[S:8][C:4]3[CH:3]=[C:2]([Cl:1])[CH:19]=[CH:18][C:5]=3[N:6]=2)=[O:17])[CH2:28]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 1519353(3S)-(+)-1-Benzyl-3-aminopyrrolidineHCID 57113159(2S)-1-(6-chloro-1,3-benzothiazol-2-yl)-2-piperidinecarboxylic acid

Product 1

HCID 57193506(2S)-N2-[(3S)-1-benzylpyrrolidin-3-yl]-1-(6-chloro-1,3-benzothiazol-2-yl)-2-piperidinecarboxamide

Procedure

The title compound was prepared by a similar method to Example 1 from (2S)-1-(6-chloro-1,3-benzothiazol-2-yl)-2-piperidinecarboxylic acid [see Preparation 45] and (3S)-1-benzylpyrrolidin-3-ylamine [see J. Med. Chem. (1989), 31(8), 1586-1590] to afford (2S)-N2-[(3S)-1-benzylpyrrolidin-3-yl]-1-(6-chloro-1,3-benzothiazol-2-yl)-2-piperidinecarboxamide as a solid.

Sources & evidence

ORD record
ord-314196501861464f9100bcaa691acd85
Source dataset
uspto-grants-2002_04
Patent number
US06372736B1

Reaction notes

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