Water → HCID 18416669, compound

HRID 2188308Notes

Reaction equation

[OH-].[Na+].[CH2:3]([N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19]([NH:21][CH:22]([CH3:27])[CH:23]=[C:24](Cl)Cl)=[O:20])=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.C(OCC)(=[O:31])C>CN1CCCC1=O>[CH2:3]([N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19]2[O:20][C:23]([CH2:24][OH:31])=[C:22]([CH3:27])[N:21]=2)=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 55 °C

Procedure

80 μl of NaOH, 1M, were added to 15 mg of 3-(1-benzylindazole-3-carboxamido)-1,1-dichlorobut-1-ene (40 μmol) in 20 μl of N-methylpyrrolidone under argon and the mixture was heated at 55° C. for 1 hour. It was cooled and 0.8 ml of water and 8 ml of ethyl acetate were added. The organic phase was concentrated and the residue was purified by preparative TLC (SiO2). 9.9 mg (77%) of 2-(1-benzylindazol-3-yl)-5-hydroxymethyl-4-methyl-oxazole were obtained (melting point 127-129° C.).

Workup

temperatureIt was cooled
concentrationThe organic phase was concentrated
customthe residue was purified by preparative TLC (SiO2)

Sources & evidence

ORD record: ord-34a157be60654346ab3b20547fccb163
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06410740B1

Reaction notes

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