N-(2-Aminoethyl)isoquinoline-5-sulfonamide → HCID 58816144, compound

HRID 2219241Notes

Reaction equation

CC(C[AlH]CC(C)C)C.CO[C:12](=O)[CH2:13][N:14]([C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=1)[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].[NH2:30][CH2:31][CH2:32][NH:33][S:34]([C:37]1[C:38]2[CH:39]=[CH:40][N:41]=[CH:42][C:43]=2[CH:44]=[CH:45][CH:46]=1)(=[O:36])=[O:35]>>[C:18]([O:17][C:15](=[O:16])[N:14]([C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=1)[CH2:13][CH2:12][NH:30][CH2:31][CH2:32][NH:33][S:34]([C:37]1[C:38]2[CH:39]=[CH:40][N:41]=[CH:42][C:43]=2[CH:44]=[CH:45][CH:46]=1)(=[O:36])=[O:35])([CH3:21])([CH3:20])[CH3:19]

Participants

Reactant 3

HCID 3544N-(2-Aminoethyl)isoquinoline-5-sulfonamide

HCID 14487Diisobutylaluminum hydride

HCID 44227926HCID 44227926, compound

Product 1

HCID 58816144HCID 58816144, compoundYield 71%

Procedure

By following similar procedure as described in Example 1, DIBAL-H reduction of [(4-bromo-phenyl)-tert-butoxycarbonyl-amino]-acetic acid methyl ester (aqueous Rochelle's salt work-up) and subsequent reductive amination with isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide gives the free amine product as a solid (71% yield). ESIMS: m/z 549 [(M+H)+, 79Br], 551 [(M+H)+, 81Br].

Sources & evidence

ORD record: ord-90ea6ccc7f0b4fd2922a2792c3a61533
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07414063B2

Reaction notes

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