1-Ethylpiperidin-4-amine → (R)-4-(9-cyclopentyl-7-fluoro-5-methyl-6-oxo-7-vinyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-N-(1-ethylpiperidin-4-yl)-3-methoxybenzamide

Participants

Role	Name	HCID	Charge
Reactant	1-Ethylpiperidin-4-amine	HCID 3734990	—
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	(R)-4-(9-cyclohexyl-7-fluoro-7-vinyl-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[5,4-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid	HCID 67117829	—
Product	(R)-4-(9-cyclopentyl-7-fluoro-5-methyl-6-oxo-7-vinyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-N-(1-ethylpiperidin-4-yl)-3-methoxybenzamide	HCID 25253227	—

Reaction Steps

The title compound was synthesized from (R)-4-(9-cyclohexyl-7-fluoro-7-vinyl-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[5,4-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid as described in the General procedure for amide bond synthesis using HATU and 4-amino 1-N-ethyl piperidine. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.47-2.04 (m, 16H) 2.32 (q, J=7.07 Hz, 3H) 2.88 (d, J=11.62 Hz, 2H) 3.28 (s, 3H) 3.67-3.87 (m, 3H) 3.94 (s, 3H) 4.87 (d, J=8.34 Hz, 1H) 5.30-5.45 (m, 2H) 6.01 (ddd, J=17.43, 12.88, 10.86 Hz, 1H) 7.46 (d, J=1.77 Hz, 2H) 7.82 (s, 1H) 8.12 (s, 2H) 8.30 (d, J=8.08 Hz, 1H). [M+H] calc'd for C30H40FN7O3, 566. found 566.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08026234B2
Source dataset	uspto-grants-2011_09
ORD ID	ord-0a29249717da4e98a56e8987aa7e359b
Source note	uspto-grants-2011_09