cis-3-(2,5-Dimethyl-benzoimidazol-1-yl)-cyclopentylamine hydrochloride → cis-(S)-(5-Bromo-indan-2-ylmethyl)-[3-(2,5-dimethyl-benzoimidazol-1-yl)-cyclopentyl]-amine

HRID 1993881Notes

Reaction equation

HRID 1993881 reaction equation
Cl.[CH3:2][C:3]1[N:7]([C@@H:8]2[CH2:12][CH2:11][C@H:10]([NH2:13])[CH2:9]2)[C:6]2[CH:14]=[CH:15][C:16]([CH3:18])=[CH:17][C:5]=2[N:4]=1.[Br:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[CH2:25][C@H:24]([CH:29]=O)[CH2:23]2>>[Br:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[CH2:25][C@H:24]([CH2:29][NH:13][C@H:10]1[CH2:11][CH2:12][C@@H:8]([N:7]3[C:6]4[CH:14]=[CH:15][C:16]([CH3:18])=[CH:17][C:5]=4[N:4]=[C:3]3[CH3:2])[CH2:9]1)[CH2:23]2

Participants

3

Reactant 2

HCID 66877495cis-3-(2,5-Dimethyl-benzoimidazol-1-yl)-cyclopentylamine hydrochlorideHCID 86620958(S)-5-bromo-indan-2-carbaldehyde

Product 1

HCID 59135487cis-(S)-(5-Bromo-indan-2-ylmethyl)-[3-(2,5-dimethyl-benzoimidazol-1-yl)-cyclopentyl]-amine

Procedure

This compound was prepared from cis-3-(2,5-dimethyl-benzoimidazol-1-yl)-cyclopentylamine hydrochloride and (S)-5-bromo-indan-2-carbaldehyde using the same reductive amination method described in previous example. 1H-NMR is consistent with the assigned structure. LC-MS showed a single peak, C24H28BrN3 (m/e) calcd 437.1467, obsd 438.1 (M+H).

Sources & evidence

ORD record
ord-c3910a3dae0f40e09961431baa424d32
Source dataset
uspto-grants-2010_01
Patent number
US07652053B2

Reaction notes

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