Ethyl 3-amino-2,2-dimethylpropanoate → HCID 89815410, compound

HRID 1481008Notes

Reaction equation

HRID 1481008 reaction equation
CO[C:3]([C:5]1[N:6]=[C:7]([C:24]#[N:25])[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][C:20]([Cl:23])=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].[NH2:26][CH2:27][C:28]([CH3:35])([CH3:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30]>CCO>[CH2:32]([O:31][C:29](=[O:30])[C:28]([CH3:35])([CH3:34])[CH2:27][NH:26][C:3]([C:5]1[N:6]=[C:7]([C:24]#[N:25])[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][C:20]([Cl:23])=[CH:19][CH:18]=1)[CH:9]=2)=[O:4])[CH3:33]

Participants

4

Reactant 2

HCID 421529Ethyl 3-amino-2,2-dimethylpropanoateHCID 89812912HCID 89812912, compound

Product 1

HCID 89815410HCID 89815410, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7-(4-Chloro-phenoxy)-1-cyano-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester (21 mg, 0.06 mmol) and ethyl 3-amino-2,2-dimethylpropanoate (34 mg, 0.24 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=8.41 (d, 1H, J=9.0 Hz), 8.32 (t, 1H, J=6.6 Hz), 7.60-7.39 (m, 4H), 7.12-7.06 (m, 2H), 4.24 (q, 2H, J=7.0 Hz), 3.61 (d, 2H, J=6.6 Hz), 1.37 (t, 3H, J=7.0 Hz), 1.30 (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-e6a10c692e5d47ceb6b2e871386b72bd
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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