Glycine → Glycine, N-[[4-hydroxy-6-(phenylthio)-3-isoquinolinyl]carbonyl]-

HRID 1406153Notes

Reaction equation

HRID 1406153 reaction equation
C(O[C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([S:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:13][CH:12]=2)=[O:7])CCC.[NH2:26][CH2:27][C:28]([OH:30])=[O:29].C[O-].[Na+]>>[OH:18][C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([S:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:15]=2)[CH:10]=[N:9][C:8]=1[C:6]([NH:26][CH2:27][C:28]([OH:30])=[O:29])=[O:7]

Participants

4

Reactant 3

HCID 750GlycineHCID 10942334Sodium MethoxideHCID 66712774HCID 66712774, compound

Product 1

HCID 11175664Glycine, N-[[4-hydroxy-6-(phenylthio)-3-isoquinolinyl]carbonyl]-

Procedure

127 mg of 4-hydroxy-6-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl ester (0.36 mmol) were reacted with glycine and sodium methylate analogously to Example D-1 g). 118 mg of the title compound were obtained; 1H NMR (DMSO-d6): δ=9.33 (t, 1 H), 8.80 (s, 1 H), 8.11 (d, 1 H), 7.79 (s, 1 H), 7.49 to 7.65 (m, 6 H), 4.01 (d, 2 H).

Sources & evidence

ORD record
ord-de1338317f4f46649a85f86b9aca6f39
Source dataset
uspto-grants-2014_12
Patent number
US08916585B2

Reaction notes

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