Hydrazine → HCID 22479786, compound

HRID 1353749Notes

Reaction equation

[CH3:1][N:2]([CH3:21])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([NH2:20])=O)[CH:16]=3)[NH:11][N:10]=2)=[CH:5][CH:4]=1.COC(OC)[N:25]([CH3:27])C.[NH2:30]N>C(O)(=O)C>[NH:30]1[C:18]([C:15]2[CH:16]=[C:17]3[C:12](=[CH:13][CH:14]=2)[NH:11][N:10]=[C:9]3[C:6]2[CH:7]=[CH:8][C:3]([N:2]([CH3:21])[CH3:1])=[CH:4][CH:5]=2)=[N:20][CH:27]=[N:25]1

Participants

Conditions

Temperature: 93 °C

Procedure

A mixture of 3-[4-(dimethylamino)phenyl]-1H-indazole-5-carboxamide (60 mg, 0.214 mmol) and N,N-dimethylformamide dimethyl acetal (10.0 mL, 75.3 mmol, 352 equiv.) was heated at 93° C. for 4.5 h and then concentrated. To the concentrate was added 4.0 mL of glacial acetic acid (AcOH), and anhydrous hydrazine (180 mg, 5.62 mmol, 26.3 equiv.). The mixture was heated at 93° C. for 3 h and concentrated. The residue was partitioned between EtOAc and 6.0 N aq. NaOH and the layers separated. The aqueous layer was extracted with 2×EtOAc and then the pH adjusted between 10–11 with 6.0 N aq. HCl. The resulting precipitate was collected by filtration, washed with H2O, and dried in a vacuum oven to afford the title compound (191 mg, 29.3% yield): 1H NMR (DMSO-d6 D2O containing one drop of aqueous HCl) δ 9.30 (s, 1H), 8.89 (s, 1H), 8.27 (d, 2H), 8.12 (d, 1H), 7.96–7.88 (m, 3H), 3.29 (s, 6H); ES-MS (m/z) 305 [M+1]+.

Workup

concentrationconcentrated
temperatureThe mixture was heated at 93° C. for 3 h
concentrationconcentrated
customThe residue was partitioned between EtOAc and 6.0 N aq. NaOH
customthe layers separated
extractionThe aqueous layer was extracted with 2×EtOAc
filtrationThe resulting precipitate was collected by filtration
washwashed with H2O
customdried in a vacuum oven

Sources & evidence

ORD record: ord-f54c6c6669f9467db0f7fe1730eb9ceb
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220771B2

Reaction notes

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