Acetic Acid → HCID 136011270, compound

HRID 1353748Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([NH2:19])=O)[CH:15]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1.COC(OC)[N:23]([CH3:25])C.C(O)(=O)C.[NH2:32]N>O>[NH:19]1[C:17]([C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[NH:10][N:9]=[C:8]3[C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)=[N:23][CH:25]=[N:32]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 3-(4-hydroxyphenyl)-1H-indazole-5-carboxamide (100 mg, 0.425 mmol) and N,N-dimethylformamide dimethyl acetal (10.0 mL, 75.3 mmol, 177 equiv.) was heated at 90° C. for 3 h. The reaction mixture was separated from some dark residue via pipet and concentrated. To the concentrate was added 20 mL of glacial acetic acid (AcOH), and anhydrous hydrazine (357 mg, 11.1 mmol, 26.1 equiv.). The mixture was heated at 90° C. for 2 h. Water (50 mL) was added to the mixture, and the acetic acid was removed on a rotary evaporator. The remaining mixture was extracted with EtOAc. The combined organics were dried (Na2SO4) and purified by prep HPLC to afford the title compound (11.4 mg, 9.7% yield): 1H NMR (DMSO-d6) δ 13.25 (br s, 1H), 9.70 (br, 2H), 8.64 (s, 1H), 8.42 (br s, 1H) 8.05 (d, 1H), 7.83 (d, 2H), 7.65 (d, 1H), 6.95 (d, 2H); ES-MS (m/z) 278 [M+1]+.

Workup

customThe reaction mixture was separated from some dark residue via pipet
concentrationconcentrated
temperatureThe mixture was heated at 90° C. for 2 h
customthe acetic acid was removed on a rotary evaporator
extractionThe remaining mixture was extracted with EtOAc
dry with materialThe combined organics were dried (Na2SO4)
custompurified by prep HPLC

Sources & evidence

ORD record: ord-1445e08a034f43f497523b27f0c78994
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220771B2

Reaction notes

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