Methyl 3-amino-2,2-dimethylpropanoate → Methyl 3-(4-hydroxy-7-(4-methoxybenzylamino)isoquinoline-3-carboxamido)-2,2-dimethylpropanoate

HRID 1481147Notes

Reaction equation

HRID 1481147 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)=[CH:9][CH:10]=2)[CH:5]=[N:4][C:3]=1[C:22](OC)=[O:23].[NH2:26][CH2:27][C:28]([CH3:34])([CH3:33])[C:29]([O:31][CH3:32])=[O:30]>CO>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)=[CH:9][CH:10]=2)[CH:5]=[N:4][C:3]=1[C:22]([NH:26][CH2:27][C:28]([CH3:34])([CH3:33])[C:29]([O:31][CH3:32])=[O:30])=[O:23]

Participants

4

Reactant 2

HCID 13285789Methyl 3-amino-2,2-dimethylpropanoateHCID 89813034Methyl 4-hydroxy-7-(4-methoxybenzylamino)isoquinoline-3-carboxylate

Product 1

HCID 89813031Methyl 3-(4-hydroxy-7-(4-methoxybenzylamino)isoquinoline-3-carboxamido)-2,2-dimethylpropanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-hydroxy-7-(4-methoxybenzylamino)isoquinoline-3-carboxylate (49.0 mg, 0.14 mmol) and methyl 3-amino-2,2-dimethylpropanoate (114.0 mg, 0.87 mmol) in MeOH (3 mL) were heated at 150° C. in a microwave for 4 hours. The solvent was removed in vacuo and the residue oil was purified by flash chromatography (0-10% EtOAc/CH2Cl2) to give the title compound in 15 mg. 1H NMR (CDCl3, 200 MHz): δ=13.10 (s, 1H), 8.40-8.28 (m, 2H), 8.10 (d, 1H, J=9.0 Hz), 7.30 (d, 2H, J=6.6 Hz), 7.05 (d, 1H, J=9.0 Hz), 6.92-6.80 (m, 3H), 5.14 (s, 1H), 4.38 (s, 2H), 3.81 (s, 3H), 3.68 (s, 3H), 3.59 (d, 2H, J=6.6 Hz), 1.28 (s, 6H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue oil was purified by flash chromatography (0-10% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-d0a4e4a63110425e96b592b259efc754
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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