Hydrazine → HCID 69670471, compound

HRID 81062Notes

Reaction equation

HRID 81062 reaction equation
[NH2:1][C:2]1[C:6]2[C:7]([C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:23][CH:22]=3)=[N:8][C:9]([C:11]3[CH:20]=[CH:19][C:14]([C:15](OC)=[O:16])=[CH:13][CH:12]=3)=[CH:10][C:5]=2[NH:4][N:3]=1.[NH2:34][NH2:35]>CN(C)C=O>[NH2:1][C:2]1[C:6]2[C:7]([C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)=[CH:23][CH:22]=3)=[N:8][C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:15]([NH:34][NH2:35])=[O:16])=[CH:19][CH:20]=3)=[CH:10][C:5]=2[NH:4][N:3]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 66926934HCID 66926934, compound

Product 1

HCID 69670471HCID 69670471, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 4-(3-amino-4-(4-phenoxyphenyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)benzoate (28 mg, 0.064 mmol, from Example 192) and hydrazine (20 μL 0.637 mmol) in N,N-dimethylformamide (0.5 mL) was stirred at 100° C. for 3 h. LC-MS showed that only small amount of the desired product was formed. A 35% aqueous solution of hydrazine (0.5 mL) was added. After additional 1 h at 100° C., the mixture was cooled to give a suspension. Water was added and the mixture filtered. The solid was washed with water, dried under vacuum to give Example 194 (19 mg, 67% yield). 1H NMR (400 MHz, methanol-d4) δ ppm 8.18 (2H, δ, J=8.53 Hz), 7.91 (2H, δ, J=8.53 Hz), 7.81-7.85 (2H, m), 7.71 (1H, s), 7.42 (2H, t, J=8.03 Hz), 7.16-7.22 (3H, m), 7.13 (2H, dd, J=8.66, 1.13 Hz); MS (ES+) m/z: 437 (M+H); LC retention time: 2.801 min (analytical HPLC Method A).

Sources & evidence

ORD record
ord-21e3c0d247a14affb46064e021cc530a
Source dataset
uspto-grants-2014_09
Patent number
US08846673B2

Reaction notes

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