1-Hydroxyisoquinoline-6-carboxylic acid → 1-(4-Methoxybenzylamino)isoquinoline-6-carboxylic acid

HRID 880974Notes

Reaction equation

HRID 880974 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16](C(O)=O)[CH:17]=3)[CH:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1.O=C1C2C(=CC([C:35]([OH:37])=[O:36])=CC=2)C=CN1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([C:35]([OH:37])=[O:36])=[CH:16][CH:17]=3)[CH:12]=[CH:11][N:10]=2)=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 582525541-Hydroxyisoquinoline-6-carboxylic acidHCID 674916931-(4-Methoxybenzylamino)isoquinoline-7-carboxylic acid

Product 1

HCID 674914271-(4-Methoxybenzylamino)isoquinoline-6-carboxylic acid

Procedure

The title compound was prepared by a method analogous to that described in Steps 2-5 of Intermediate 27, using 1-oxo-1,2-dihydroisoquinoline-6-carboxylic acid. +ESI (M+H) 309.2; 1H NMR (400 MHz, CD3OD, δ): 8.37 (d, J=1.56 Hz, 1H), 8.34 (d, J=8.78 Hz, 1H), 8.12 (dd, J=8.68, 1.66 Hz, 1H), 7.67 (d, J=6.44 Hz, 1H), 7.29-7.36 (m, 2H), 7.15 (d, J=6.24 Hz, 1H), 6.86-6.93 (m, 2H), 4.73 (s, 2H), 3.76 (s, 3H).

Sources & evidence

ORD record
ord-5fdd0faabbb5454dbd70cbd63c3553dd
Source dataset
uspto-grants-2015_03
Patent number
US08993586B2

Reaction notes

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