Ethyl 3-amino-2,2-dimethylpropanoate → HCID 89813132, compound

HRID 1481002Notes

Reaction equation

HRID 1481002 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([OH:21])=[C:10]([C:17](OC)=[O:18])[N:11]=[C:12]2[C:15]#[N:16])=[CH:7][CH:6]=1.[NH2:26][CH2:27][C:28]([CH3:35])([CH3:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30]>CCO>[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([OH:21])=[C:10]([C:17]([NH:26][CH2:27][C:28]([CH3:35])([CH3:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:18])[N:11]=[C:12]2[C:15]#[N:16])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 421529Ethyl 3-amino-2,2-dimethylpropanoateHCID 89813044HCID 89813044, compound

Product 1

HCID 89813132HCID 89813132, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 7-(2-chlorophenoxy)-1-cyano-4-hydroxyisoquinoline-3-carboxylate (20 mg, 0.06 mmol) and ethyl 3-amino-2,2-dimethylpropanoate (33 mg, 0.23 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 30 mg. 1H NMR (CDCl3, 200 MHz): δ=8.41 (d, 1H, J=8.5 Hz), 8.30 (t, 1H, J=6.6 Hz), 7.57-7.48 (m, 2H), 7.42-7.17 (m, 4H), 4.23 (q, 2H, J=7.0 Hz), 3.60 (d, 2H, J=6.6 Hz), 1.35 (t, 3H, J=7.0 Hz), 1.28 (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-055ea2e92ed149acb042b6537368d7e8
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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