trans-3-(5-fluoro-1H-indol-3-yl)-cyclopentylamine → N-{[(2S)-8-ethoxy-2,3-dihydro-1,4-benzodioxin-2-yl]methyl}-N-[(trans)-3-(5-fluoro-1H-indol-3-yl)cyclopentyl]amine

HRID 1724705Notes

Reaction equation

HRID 1724705 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]2[O:18][C:17]3[C:19]([O:23][CH2:24][CH3:25])=[CH:20][CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=O)=O)=CC=1.[F:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][CH:31]=[C:30]2[C@H:36]1[CH2:40][CH2:39][C@H:38]([NH2:41])[CH2:37]1>>[CH2:24]([O:23][C:19]1[C:17]2[O:18][C@@H:13]([CH2:12][NH:41][C@H:38]3[CH2:39][CH2:40][C@H:36]([C:30]4[C:29]5[C:33](=[CH:34][CH:35]=[C:27]([F:26])[CH:28]=5)[NH:32][CH:31]=4)[CH2:37]3)[CH2:14][O:15][C:16]=2[CH:22]=[CH:21][CH:20]=1)[CH3:25]

Participants

3

Reactant 2

HCID 68827696trans-3-(5-fluoro-1H-indol-3-yl)-cyclopentylamineHCID 86593209[(2R)-8-ethoxy-2,3-dihydro-benzo[1,4]dioxin-2-yl]methyl 4-methylbenzenesulfonate

Product 1

HCID 68827559N-{[(2S)-8-ethoxy-2,3-dihydro-1,4-benzodioxin-2-yl]methyl}-N-[(trans)-3-(5-fluoro-1H-indol-3-yl)cyclopentyl]amineYield 64%

Procedure

This compound was prepared in the same manner as for Example 1, using [(2R)-8-ethoxy-2,3-dihydro-benzo[1,4]dioxin-2-yl]methyl 4-methylbenzenesulfonate (0.25 g, 0.68 mmol) and trans-3-(5-fluoro-1H-indol-3-yl)-cyclopentylamine (0.3 g, 1.38 mmol) to afford 0.16 g (64%) of the title compound as its hydrochloride salt: MS (ESI) m/z 411 [M+H]+.

Workup

  1. customThis compound was prepared in the same manner as for Example 1

Sources & evidence

ORD record
ord-8e465a34c6994409a6163333c17739a3
Source dataset
uspto-grants-2009_02
Patent number
US07488751B2

Reaction notes

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