N-(2-Aminoethyl)isoquinoline-5-sulfonamide → HCID 131726993, compound

HRID 2219225Notes

Reaction equation

HRID 2219225 reaction equation
CC(C[AlH]CC(C)C)C.[Cl:10][C:11]1[CH:20]=[CH:19][C:14]([O:15][CH2:16][C:17]#[N:18])=[CH:13][CH:12]=1.N[CH2:22][CH2:23][NH:24][S:25]([C:28]1[C:29]2[CH:30]=[CH:31][N:32]=[CH:33][C:34]=2[CH:35]=[CH:36][CH:37]=1)(=[O:27])=[O:26]>>[ClH:10].[ClH:10].[Cl:10][C:11]1[CH:20]=[CH:19][C:14]([O:15][CH2:16][CH2:17][NH:18][CH2:22][CH2:23][NH:24][S:25]([C:28]2[C:29]3[CH:30]=[CH:31][N:32]=[CH:33][C:34]=3[CH:35]=[CH:36][CH:37]=2)(=[O:26])=[O:27])=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 3544N-(2-Aminoethyl)isoquinoline-5-sulfonamideHCID 14487Diisobutylaluminum hydrideHCID 3064442-(4-Chlorophenoxy)acetonitrile

Product 1

HCID 131726993HCID 131726993, compound

Procedure

By following similar procedure as described in Example 31, DIBAL-H reduction of (4-chloro-phenoxy)-acetonitrile and subsequent reductive amination with isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide gives the free amine product as oil. The free amine is converted to the di-hydrochloride salt of the title compound as a hygroscopic white powder. ESIMS: m/z 406 [(M+H)+, 35Cl], 408 [(M+H)+, 37Cl].

Sources & evidence

ORD record
ord-c0ca4240328f46439812b02041783e50
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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