Isoquinoline-3-carboxylic acid → 2,3-Diaminobenzoic acid methyl ester

HRID 1844943Notes

Reaction equation

HRID 1844943 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[C:5]=1[NH2:13].[CH:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[C:17]([C:25](O)=[O:26])[N:16]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=1[NH2:13].[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:25]([C:17]2[N:16]=[CH:15][C:24]3[C:19]([CH:18]=2)=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:26])[C:5]=1[NH2:13]

Participants

5

Reactant 3

HCID 124656Isoquinoline-3-carboxylic acidHCID 607264Methyl 2-amino-3-nitrobenzoateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 2

HCID 5718252,3-Diaminobenzoic acid methyl esterHCID 669403142-Amino-3-[(isoquinoline-3-carbonyl)-amino]-benzoic acid methyl ester

Procedure

The 2,3-diamino-benzoic acid methyl ester was synthesized from 2-amino-3-nitro-benzoic acid methyl ester (2.0 g, 10.2 mmol) as described in general procedure C. 1.7 g (10.2 mmol) of the above synthesized diamine was reacted with 1.7 g (10.0 mmol) of isoquinoline-3-carboxylic acid and 4.6 g (12.0 mmol) of HBTU as described in general procedure A to provide 2-amino-3-[(isoquinoline-3-carbonyl)-amino]-benzoic acid methyl ester. LCMS: 322 (M+1)+.

Sources & evidence

ORD record
ord-c8f283f1b66446b38efbc59bf7da5dfe
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

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