N-(2-Aminoethyl)isoquinoline-5-sulfonamide → Isoquinoline-5-sulfonic acid {2-[2-(4-chloro-2-(3-trifluoromethyl-benzyl)-phenyloxy)-ethylamino]-ethyl}-amide

HRID 2219239Notes

Reaction equation

HRID 2219239 reaction equation
CC(C[AlH]CC(C)C)C.CO[C:12](=O)[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=1.[NH2:34][CH2:35][CH2:36][NH:37][S:38]([C:41]1[C:42]2[CH:43]=[CH:44][N:45]=[CH:46][C:47]=2[CH:48]=[CH:49][CH:50]=1)(=[O:40])=[O:39]>>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][CH2:12][NH:34][CH2:35][CH2:36][NH:37][S:38]([C:41]2[C:42]3[CH:43]=[CH:44][N:45]=[CH:46][C:47]=3[CH:48]=[CH:49][CH:50]=2)(=[O:40])=[O:39])=[C:16]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=2)[CH:17]=1

Participants

4

Reactant 3

HCID 3544N-(2-Aminoethyl)isoquinoline-5-sulfonamideHCID 14487Diisobutylaluminum hydrideHCID 69273829[4-Chloro-2-(3-trifluoromethyl-benzyl)-phenyloxy]-acetic acid methyl ester

Product 1

HCID 58816176Isoquinoline-5-sulfonic acid {2-[2-(4-chloro-2-(3-trifluoromethyl-benzyl)-phenyloxy)-ethylamino]-ethyl}-amide

Procedure

By following a similar procedure as described in Example 1, DIBAL-H reduction of [4-chloro-2-(3-trifluoromethyl-benzyl)-phenyloxy]-acetic acid methyl ester, and subsequent reductive amination with isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide gives the free amine of the title compound as a clear gum. ESIMS: m/z 564 [(M+H)+, 35Cl], 566 [(M+H)+, 37Cl].

Sources & evidence

ORD record
ord-a80dea2fdb724007a5b897d20aefa444
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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