Hydrazine hydrate (1:1) → HCID 25121734, compound

HRID 2189171Notes

Reaction equation

F[C:2]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][CH2:23][CH:24]([CH3:26])C)[NH:13][C:12](=[O:27])[CH:11]=2)=[CH:6][C:3]=1[C:4]#[N:5].O.[NH2:29][NH2:30]>C(O)C>[NH2:5][C:4]1[C:3]2[C:2](=[CH:9][CH:8]=[C:7]([C:10]3[CH:15]=[C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[O:22][CH2:23][CH2:24][CH3:26])[NH:13][C:12](=[O:27])[CH:11]=3)[CH:6]=2)[NH:30][N:29]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-fluoro-5-(6-{2-[(2-methylpropyl)oxy]phenyl}-2-oxo-1,2-dihydropyridin-4-yl)benzonitrile (50 mg), and hydrazine hydrate (2 mL) in ethanol (10 mL)was heated to 100° C. for 3 h. The reaction mixture was concentrated and the product was purified by preparative HPLC (reverse-phase, acetonitrile/water with 0.01% ammonium acetate) to afford 4-(3-amino-1H-indazol-5-yl)-6-[2-(propyloxy)phenyl]pyridin-2(1H)-one (20 mg). 1H NMR (400 MHz, d4-CD3OD): δ 8.18 (s, 1H), 7.72 (d, 1H), 7.57 (d, 1H), 7.46 (t, 1H), 7.39 (d, 1H), 7.16-7.08 (m, 2H), 6.92 (d, 1H), 6.76 (s, 1H), 3.88 (d, 2H), 2.12-2.05 (m, 1H), 1.00 (d, 6H). MS (EI) for C22H22N4O2: 375 (MH±).

Workup

concentrationThe reaction mixture was concentrated
customthe product was purified by preparative HPLC (reverse-phase, acetonitrile/water with 0.01% ammonium acetate)

Sources & evidence

ORD record: ord-cafd81556a9243b59e09cb724b44b4cc
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324231B2

Reaction notes

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