Dimethylamine → 2-(3-((3-Amino-4-(4-phenoxyphenyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)amino)-1H-pyrazol-1-yl)-N,N-dimethylacetamide

Participants

Role	Name	HCID	Charge
Reactant	Dimethylamine	HCID 674	—
Reactant	Hydrazine	HCID 9321	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	2-(3-(4-chloro-5-cyano-6-(4-phenoxyphenyl)pyridin-2-ylamino)-1H-pyrazol-1-yl)acetic acid	HCID 66927188	—
Product	2-(3-((3-Amino-4-(4-phenoxyphenyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)amino)-1H-pyrazol-1-yl)-N,N-dimethylacetamide	HCID 69670483	—

Reaction Steps

The acid from Step 2 of Example 248 and dimethylamine were coupled with HATU and subsequently reacted with hydrazine following conditions in Step 3 of Example 248 to give Example 249. 1H NMR (400 MHz, methanol-d4) δ ppm 7.91-7.97 (2H, m), 7.65 (1H, d, J=2.51 Hz), 7.47-7.54 (2H, m), 7.31 (1H, t, J=7.40 Hz), 7.18-7.24 (4H, m), 6.78 (1H, s), 6.05 (1H, d, J=2.26 Hz), 5.09 (2H, s), 3.03 (3H, s), 2.86 (3H, s); MS (ES+) m/z: 469.5 (M+H); LC retention time: 3.238 min (analytical HPLC

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08846673B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-16054371714e4b4c803d24d1b6f073d4
Source note	uspto-grants-2014_09