N-(2-Aminoethyl)isoquinoline-5-sulfonamide → HCID 131726994, compound

HRID 2219228Notes

Reaction equation

HRID 2219228 reaction equation
CC(C[AlH]CC(C)C)C.C[O:11][C:12](=[O:26])[CH2:13][O:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([Cl:25])=[CH:17][CH:16]=1.[NH2:27][CH2:28][CH2:29][NH:30][S:31]([C:34]1[C:35]2[CH:36]=[CH:37][N:38]=[CH:39][C:40]=2[CH:41]=[CH:42][CH:43]=1)(=[O:33])=[O:32]>>[C:13]([OH:32])(=[O:14])[C:12]([OH:11])=[O:26].[C:13]([OH:32])(=[O:14])[C:12]([OH:11])=[O:26].[Cl:25][C:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15]([O:14][CH2:13][CH2:12][NH:27][CH2:28][CH2:29][NH:30][S:31]([C:34]2[C:35]3[CH:36]=[CH:37][N:38]=[CH:39][C:40]=3[CH:41]=[CH:42][CH:43]=2)(=[O:33])=[O:32])=[CH:16][CH:17]=1

Participants

4

Reactant 3

HCID 3544N-(2-Aminoethyl)isoquinoline-5-sulfonamideHCID 14487Diisobutylaluminum hydrideHCID 302909methyl 2-(4-chloronaphthalen-1-yl)oxyacetate

Product 1

HCID 131726994HCID 131726994, compound

Procedure

By following similar procedure as described in Example 34, DIBAL-H reduction of (4-chloro-naphthalen-1-yloxy)-acetic acid methyl ester and subsequent reductive amination with isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide gives the free amine product as a gum. The free amine is converted to the di-oxalic acid salt of the title compound as a white powder. ESIMS: m/z 456 [(M+H)+, 35Cl], 458 [(M+H)+, 37Cl].

Sources & evidence

ORD record
ord-666d351feb5b43afba5d361b6fdceb4c
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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