N-(2-Aminoethyl)isoquinoline-5-sulfonamide → HCID 131726992, compound
Reaction equation
CC(C[AlH]CC(C)C)C.C[O:11][C:12](=[O:22])[CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21].[NH2:23][CH2:24][CH2:25][NH:26][S:27]([C:30]1[C:31]2[CH:32]=[CH:33][N:34]=[CH:35][C:36]=2[CH:37]=[CH:38][CH:39]=1)(=[O:29])=[O:28]>>[C:13]([OH:28])(=[O:14])[C:12]([OH:11])=[O:22].[C:13]([OH:28])(=[O:14])[C:12]([OH:11])=[O:22].[Cl:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[O:14][CH2:13][CH2:12][NH:23][CH2:24][CH2:25][NH:26][S:27]([C:30]1[C:31]2[CH:32]=[CH:33][N:34]=[CH:35][C:36]=2[CH:37]=[CH:38][CH:39]=1)(=[O:29])=[O:28]Participants
Procedure
By following the procedure as described in Example 1, DIBAL-H reduction of (2-chloro-phenoxy)-acetic acid methyl ester and subsequent reductive amination with isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide (175 mg, 0.696 mmol) give 183 mg (0.451 mmol, 65% yield) of the free amine product as oil. The free amine is dissolved in EtOAc (10 mL) and treated dropwise with an EtOAc solution (10 mL) containing oxalic acid dihydrate (114 mg, 0.902 mmol) with stirring under nitrogen. The white suspension is stirred for 15 minutes, filtered and dried under vacuum at 60° C. to give 220 mg (0.375 mmol, 83% yield) of the title compound as a white powder. ESIMS: m/z 406 [(M+H)+, 35Cl], 408 [(M+H)+, 37Cl]. Analysis for C19H20ClN3O3S.1.8C2H2O4: calcd: C, 47.79; H, 4.19; N, 7.40; found: C, 47.70; H, 4.03; N, 7.45.
Sources & evidence
- ORD record
- ord-ef45b598bd9447658b805b35330d8cdf
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07414063B2
Reaction notes
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