Sodium Methoxide → HCID 89814593, compound

HRID 1481151Notes

Reaction equation

C(O[C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([S:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:12]=2)=[O:7])CCC.OC(C(F)(F)F)=O.[NH2:33][CH2:34][C:35]([CH3:40])([CH3:39])[C:36]([OH:38])=[O:37].C[O-].[Na+]>CCO>[OH:18][C:17]1[C:16]2[C:11](=[CH:12][C:13]([S:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9][C:8]=1[C:6]([NH:33][CH2:34][C:35]([CH3:40])([CH3:39])[C:36]([OH:38])=[O:37])=[O:7]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl ester (60 mg, 0.17 mmol) (prepared according to WO 2004108681), 3-amino-2,2-dimethyl-propionic acid TFA salt (157 mg, 0.68 mmol) and NaOMe (73 mg, 1.36 mmol) in EtOH (2 mL) was heated at 150° C. in a microwave reactor for 6 h. The solvent was evaporated, and the residue was partitioned between water and EtOAc. 1 M HCl was added with vigorous stirring until pH was ˜2. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by column chromatography (0-30% EtOAc/hexanes+2% AcOH) to give 18 mg of the title compound as a yellow solid. MS: (+) m/z 397.11 (M+1).

Workup

customThe solvent was evaporated
customthe residue was partitioned between water and EtOAc
addition1 M HCl was added
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated
customThe crude product was purified by column chromatography (0-30% EtOAc/hexanes+2% AcOH)

Sources & evidence

ORD record: ord-20df1371fb8d4013a10893c0212da933
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409892B2

Reaction notes

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