Ethyl 3-amino-2,2-dimethylpropanoate → HCID 89812841, compound

HRID 1481056Notes

Reaction equation

HRID 1481056 reaction equation
CO[C:3]([C:5]1[N:6]=[C:7]([C:25]#[N:26])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH3:24])[CH:9]=2)=[O:4].[NH2:27][CH2:28][C:29]([CH3:36])([CH3:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31]>CCO>[CH2:33]([O:32][C:30](=[O:31])[C:29]([CH3:36])([CH3:35])[CH2:28][NH:27][C:3]([C:5]1[N:6]=[C:7]([C:25]#[N:26])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH3:24])[CH:9]=2)=[O:4])[CH3:34]

Participants

4

Reactant 2

HCID 421529Ethyl 3-amino-2,2-dimethylpropanoateHCID 89812985HCID 89812985, compound

Product 1

HCID 89812841HCID 89812841, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Cyano-4-hydroxy-7-(2-methoxy-phenoxy)-isoquinoline-3-carboxylic acid methyl ester (23 mg, 0.07 mmol) and ethyl 3-amino-2,2-dimethylpropanoate (38 mg, 0.26 mmol) in EtOH (3 mL) were heated at 150° C. in a microwave for 1.5 hours. The solvent was removed in vacuo and the residue oil was purified by flash chromatography (0-50% EtOAc/hexanes) to give the title compound in 20 mg. 1H NMR (CDCl3, 200 MHz): δ=8.36 (d, 1H, J=9.0 Hz), 8.29 (t, 1H, J=6.2 Hz), 7.55-7.47 (m, 1H), 7.42-7.39 (m, 1H), 7.33-7.22 (m, 1H), 7.20-6.98 (m, 3H), 4.23 (q, 2H, J=7.0 Hz), 3.80 (s, 3H), 3.60 (d, 2H, J=6.2 Hz), 1.36 (t, 3H, J=7.0 Hz), 1.29 (s, 6H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue oil was purified by flash chromatography (0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-56653957f14245f4ac117c4816177272
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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