Sodium Methoxide → HCID 131736618, compound

HRID 1481078Notes

Reaction equation

HRID 1481078 reaction equation
C[O:2][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]=1OC)[CH:9]=2)=O.Cl.[NH2:28][CH2:29][C@@:30]([OH:35])([CH3:34])[C:31]([OH:33])=[O:32].[CH3:36][O-].[Na+]>CO>[C:25]([C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:9]=2)[C:14]([OH:15])=[C:5]([C:3]([NH:28][CH2:29][C@@:30]([OH:35])([CH3:34])[C:31]([O:33][CH3:36])=[O:32])=[O:2])[N:6]=1)#[N:26]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 89812985HCID 89812985, compoundHCID 89813085HCID 89813085, compound

Product 1

HCID 131736618HCID 131736618, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 1-cyano-4-hydroxy-7-(2-methoxy-phenoxy)-isoquinoline-3-carboxylic acid methyl ester (20 mg, 0.06 mmol), (S)-3-amino-2-hydroxy-2-methylpropanoic acid hydrochloride (20 mg, 0.13 mmol) and NaOMe (14 mg, 0.25 mmol) in MeOH (2 mL) was heated at 140° C. in a microwave for 2 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 9 mg. 1H NMR (CDCl3, 200 MHz): δ=13.78 (s, 1H), 8.39 (d, 1H, J=9.8 Hz), 8.20 (t, 1H, J=5.9 Hz), 7.60-7.42 (m, 4H), 7.32-7.24 (m, 1H), 7.18-7.12 (m, 2H), 4.11-3.93 (m, 1H), 3.82 (s, 3H), 3.61-3.51 (m, 2H), 1.50 (s, 3H).

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-b59e912ddc634624a55895236cb04bd0
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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