N-(2-Aminoethyl)isoquinoline-5-sulfonamide → Isoquinoline-5-sulfonic acid {2-[2-(2-bromo-4-fluoro-phenyloxy)-ethylamino]-ethyl}-amide

HRID 2219237Notes

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]([F:21])=[CH:17][C:16]=1[Br:22].[NH2:24][CH2:25][CH2:26][NH:27][S:28]([C:31]1[C:32]2[CH:33]=[CH:34][N:35]=[CH:36][C:37]=2[CH:38]=[CH:39][CH:40]=1)(=[O:30])=[O:29]>>[Br:22][C:16]1[CH:17]=[C:18]([F:21])[CH:19]=[CH:20][C:15]=1[O:14][CH2:13][CH2:12][NH:24][CH2:25][CH2:26][NH:27][S:28]([C:31]1[C:32]2[CH:33]=[CH:34][N:35]=[CH:36][C:37]=2[CH:38]=[CH:39][CH:40]=1)(=[O:30])=[O:29]

Participants

Reactant 3

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

HCID 14487Diisobutylaluminum hydride

HCID 28825613Methyl 2-(2-bromo-4-fluorophenoxy)acetate

Product 1

HCID 58816145Isoquinoline-5-sulfonic acid {2-[2-(2-bromo-4-fluoro-phenyloxy)-ethylamino]-ethyl}-amide

Procedure

By following a similar procedure as described in Example 1, DIBAL-H reduction of (2-bromo-4-fluoro-phenoxy)-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 white foam. ESIMS: m/z 468 [(M+H)+, 79Br], 470 [(M+H)+, 81Br].

Sources & evidence

ORD record: ord-370a25846a6447a999db10b3efb1ecb3
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07414063B2

Reaction notes

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