N,N-Dimethyl-1,3-propanediamine → HCID 25254308, compound

Participants

Role	Name	HCID	Charge
Reactant	N,N-Dimethyl-1,3-propanediamine	HCID 7993	—
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 25254308	HCID 25254308	—

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 N,N-dimethyl-1,3-propanediamine. The final compound was purified by reverse phase HPLC and basified to give the free base. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.14-1.49 (m, 3 H) 1.53-1.87 (m., 9 H) 2.13 (s, 6 H) 2.25 (t, J=6.44 Hz, 2 H) 3.29 (m, 2 H) 3.31 (s, 3 H) 3.93 (s, 3 H) 4.06 (t, J=13.26 Hz, 2 H) 4.46 (m, 1 H) 7.46 (d, J=8.0 Hz, 1 H) 7.51 (s, 1 H) 7.90 (s, 1 H) 8.21 (s, 1 H) 8.27 (d, J=8.08 Hz, 1 H) 8.48 (br. s., 1 H). [M+H] calculated for C27H37F2N7O3, 546; found 546.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08318727B2
Source dataset	uspto-grants-2012_11
ORD ID	ord-48598b13108b4e7d98f2316000b5e8cf
Source note	uspto-grants-2012_11