(3S)-1-(3-pyridinylmethyl)pyrrolidine-3-amine → (2S)-1-(1,3-benzothiazol-2-yl)-N-[(3S)-1-(3-pyridinylmethyl)pyrrolidin-3-yl]-2-piperidinecarboxamide

HRID 412652Notes

Reaction equation

HRID 412652 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[C:16]([OH:18])=O.[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][N:26]2[CH2:30][CH2:29][C@H:28]([NH2:31])[CH2:27]2)[CH:20]=1>CN(C)C1C=CN=CC=1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[C:16]([NH:31][C@H:28]1[CH2:29][CH2:30][N:26]([CH2:25][C:21]2[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=2)[CH2:27]1)=[O:18]

Participants

4

Reactant 2

HCID 28360955(3S)-1-(3-pyridinylmethyl)pyrrolidine-3-amineHCID 30121374(2S)-1-(1,3-benzothiazol-2-yl)-2-piperidinecarboxylic acid

Product 1

HCID 57126240(2S)-1-(1,3-benzothiazol-2-yl)-N-[(3S)-1-(3-pyridinylmethyl)pyrrolidin-3-yl]-2-piperidinecarboxamide

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

The title compound was prepared by a similar method to Example 1, excepting that a catalytic amount of 4-dimethylaminopyridine was also used, from (2S)-1-(1,3-benzothiazol-2-yl)-2-piperidinecarboxylic acid [see Preparation 43] and (3S)-1-(3-pyridinylmethyl)pyrrolidine-3-amine [see Preparation 41] to afford (2S)-1-(1,3-benzothiazol-2-yl)-N-[(3S)-1-(3-pyridinylmethyl)pyrrolidin-3-yl]-2-piperidinecarboxamide as a white solid.

Sources & evidence

ORD record
ord-3177fd2bef1e434c9f26fbd995149638
Source dataset
uspto-grants-2003_05
Patent number
US06562964B1

Reaction notes

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