1-Amino-4-methylpiperazine → 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)-3-methoxy-N-(4-methylpiperazin-1-yl)benzamide

Participants

Role	Name	HCID	Charge
Reactant	1-Amino-4-methylpiperazine	HCID 81349	—
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	HCID 67117825	HCID 67117825	—
Product	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)-3-methoxy-N-(4-methylpiperazin-1-yl)benzamide	HCID 25253071	—

Reaction Steps

The title compound was synthesized from 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 1-amino 4-methylpiperazine. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.48-2.05 (m, 8 H) 2.22 (br. s., 3 H) 2.42 (m, 4 H) 2.93 (t, J=4.55 Hz, 4 H) 3.28 (br. s., 3 H) 3.72 (m, 2 H) 3.93 (br. s., 3 H) 4.87 (m, 1 H) 5.39 (d, 2 H) 5.99 (m, 1 H) 7.43 (br. s, 2 H) 7.82 (s, 1 H) 8.12 (br. s., 1 H) 8.32 (d, J=8.0 Hz, 1 H) 9.36 (s, 1 H). Melting point: 253-263° C. [M+H] calculated for C28H37FN8O3, 553; found 553.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08318727B2
Source dataset	uspto-grants-2012_11
ORD ID	ord-8e9208ffd6284051989ef6117dc57fb5
Source note	uspto-grants-2012_11