Water → HCID 67962963, compound

HRID 1426276Notes

Reaction equation

B1([O-])OO1.[OH2:5].[OH2:6].O.O.[Na+].[NH2:10][C:11]1[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:14]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:13]([CH3:28])[N:12]=1.O>FC(F)(F)C(O)=O>[CH2:21]([C:14]1[N:13]([CH3:28])[N:12]=[C:11]([N+:10]([O-:6])=[O:5])[C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of sodium perborate tetrahydrate (95%, 3.12 g, 19.3 mmol) and trifluoroacetic acid (10 mL) was heated to 75° C. To this was added a solution of ethyl 3-amino-5-benzyl-1-methyl-1H-pyrazole-4-carboxylate (prepared according to the method of Y. Xia et al., J. Med. Chem. 1997, 40, 4372-4377; 1.00 g, 3.86 mmol) in trifluoroacetic acid, and the mixture was allowed to react at 75° C. for 2.5 hours. The reaction was then cooled, poured into water and extracted with EtOAc. The combined organic layers were washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo; purification via silica gel chromatography (Eluant: 30% EtOAc in heptane) provided C20 as a dark yellow oil. Yield: 333 mg, 1.15 mmol, 30%. LCMS m/z 290.2 (M+1). 1H NMR (400 MHz, CDCl3) δ 1.32 (t, J=7.1 Hz, 3H), 3.74 (s, 3H), 4.33 (br s, 2H), 4.34 (q, J=7.1 Hz, 2H), 7.14-7.18 (m, 2H), 7.25-7.30 (m, 1H), 7.31-7.36 (m, 2H).

Workup

customprepared
customto react at 75° C. for 2.5 hours
temperatureThe reaction was then cooled
extractionextracted with EtOAc
washThe combined organic layers were washed with water
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
custompurification via silica gel chromatography (Eluant: 30% EtOAc in heptane)
customprovided C20 as a dark yellow oil

Sources & evidence

ORD record: ord-ed66cfe21f464238a5668e4100de3bd5
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933095B2

Reaction notes

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