Ammonia → 6-(4-iodophenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide

HRID 497431Notes

Reaction equation

[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][C:11]3[C:14]([C:25]([O:27]CC)=O)=[N:15][N:16]([C:17]4[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=4)[C:10]=3[C:9]2=[O:30])=[CH:4][CH:3]=1.O.[NH3:32]>C(O)CO>[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][C:11]3[C:14]([C:25]([NH2:32])=[O:27])=[N:15][N:16]([C:17]4[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=4)[C:10]=3[C:9]2=[O:30])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 85 °C

Procedure

Ethyl 6-(4-iodophenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate from Part B of example 6 (3.0 g, 5.8 mmol) was suspended in 8% NH3 in ethylene glycol (30 mL) in a 100 mL pressure tube. The mixture was heated at 85° C. for 18 hours. Water was added, and the precipitate was filtered and washed with water. The crude product was dried under vacuum to afford 3.2 g of final product. MS (ES+): 489.2 (M+H)+. 1HNMR (DMSO-d6) δ 7.72-7.68 (m, 3H), 7.49-7.41 (m, 3H), 7.15 (d, 2H), 6.97 (d, 2H), 4.00 (t, 2H), 3.77 (s, 3H), 3.16 (t, 2H) ppm.

Workup

filtrationthe precipitate was filtered
washwashed with water
dry with materialThe crude product was dried under vacuum

Sources & evidence

ORD record: ord-bcb9584a537e4d12b5725c3cc20d7437
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949550B2

Reaction notes

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