Methylamine → HCID 25254459, compound

Participants

Role	Name	HCID	Charge
Reactant	Methylamine	HCID 6329	—
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	4-(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-benzoic acid	HCID 25253680	—
Product	HCID 25254459	HCID 25254459	—

Reaction Steps

The title compound was synthesized from 4-(9-cyclohexyl-7,7-difluoro-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 methylamine. The final compound was purified by reverse phase HPLC and basified to give the free base. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.13-1.42 (m, 2 H) 1.52-1.91 (m, 8 H) 2.80 (d, 3 H) 3.94 (s, 3 H) 4.16 (t, 2 H) 4.49 (quin, 1 H) 7.50 (d, 1 H) 7.55 (s, 1 H) 8.14 (d, J=8.1 Hz, 1 H) 8.24 (d, J=2.0 Hz, 1 H) 8.42 (d, J=4.3 Hz, 1 H) 8.58 (br. s., 1 H). [M+H] calc'd for C23H28F2N6O3 475; found 475.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08318727B2
Source dataset	uspto-grants-2012_11
ORD ID	ord-686ca13a45774a31bb2cd31aec63bb73
Source note	uspto-grants-2012_11