(1R,2R)-2-Aminocyclohexanol → HCID 25254157, compound

Participants

Role	Name	HCID	Charge
Reactant	(1R,2R)-2-Aminocyclohexanol	HCID 735777	—
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 25254157	HCID 25254157	—

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 trans-(±)-2-aminocyclohexanol. The final compound was purified by reverse phase HPLC and basified to give the free base. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.11-1.93 (m, 18 H) 3.32 (s, 1 H) 3.45 (m, 1 H) 3.64 (m, 1 H) 3.95 (s, 3 H) 4.07 (t, J=13.39 Hz, 2 H) 4.48 (m, 1 H) 4.64 (br. s., 1 H) 7.49 (d, J=8.0 Hz, 1 H) 7.55 (s, 1 H) 7.90 (s, 1 H) 8.03 (d, J=8.08 Hz, 1 H) 8.22 (s, 1 H) 8.28 (d, J=8.34 Hz, 1 H). [M+H] calculated for C28H36F2N6O4, 559; found 559.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08318727B2
Source dataset	uspto-grants-2012_11
ORD ID	ord-7eb984e356494700bcaa0bcf1c637cba
Source note	uspto-grants-2012_11