N,N'-Dimethylethylenediamine → HCID 86703902, compound

Participants

Role	Name	HCID	Charge
Reactant	N,N'-Dimethylethylenediamine	HCID 8070	—
Reactant	Diisopropylethylamine	HCID 81531	—
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	3-(4-Aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzoic acid	HCID 72703520	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 86703902	HCID 86703902	—

Reaction Steps

Following the same reaction and purification procedure, the acid 3 (100 mg, 0.35 mmol) was reacted with N,N′-dimethylethane-1,2-diamine (CAS 5752-40-9) (0.08 mL, 0.7 mmol), HATU (165 mg, 0.42 mmol) and DIPEA (0.30 mL, 1.8 mmol) in DMF (1 mL) at room temperature to provide 3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-N-(2-(dimethylamino)ethyl)-5-fluorobenzamide 12. LC/MS (ESI+): m/z 355 (M+H). 1H NMR (400 MHz, DMSO) δ 8.69 (t, J=5.5 Hz, 1H), 8.62 (d, J=8.8 Hz, 1H), 8.57 (dd, J=19.4, 10.5 Hz, 2H), 8.44 (s, 1H), 8.27 (d, J=8.8 Hz, 1H), 8.20 (d, J=8.8 Hz, 1H), 8.05 (s, 1H), 7.73 (d, J=9.3 Hz, 1H), 3.43 (dd, J=12.8, 6.6 Hz, 2H), 2.46 (t, J=6.9 Hz, 2H), 2.21 (s, 6H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09382241B2
Source dataset	uspto-grants-2016_07
ORD ID	ord-690818fb17a34a88b16adb2306100368
Source note	uspto-grants-2016_07