Sodium Methoxide → HCID 89812930, compound

HRID 1481080Notes

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]=1OC)[CH:9]=2)=[O:4].Cl.[NH2:28][C@H:29]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C@H:30]([OH:34])[C:31]([OH:33])=[O:32].[CH3:42][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][C@H:29]([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C@H:30]([OH:34])[C:31]([O:33][CH3:42])=[O:32])=[O:4])[N:6]=1)#[N:26]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 1-cyano-4-hydroxy-7-(2-methoxy-phenoxy)-isoquinoline-3-carboxylic acid methyl ester (15 mg, 0.05 mmol), (2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid hydrochloride (40 mg, 0.17 mmol) (Yuan et al. (1993) J Med Chem 36:211-220) and NaOMe (18 mg, 0.33 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 (0-10% EtOAc/CH2Cl2) to give the title compound in 4 mg. MS: (−) m/z 496.14 (M−1).

Workup

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

Sources & evidence

ORD record: ord-a43ea83dbfb54c6598b55c1b5f0f5bbf
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409892B2

Reaction notes

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