Hydrochloric Acid → 2-{[5-(3-aminopropyl)-2-methylpyridin-3-yl]amino}-9-(trifluoromethyl)-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one

HRID 2387988Notes

Reaction equation

HRID 2387988 reaction equation
Cl.[CH3:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][NH:12]C(=O)OC(C)(C)C)=[CH:5][C:4]=1[NH:20][C:21]1[N:22]=[CH:23][C:24]2[CH2:25][C:26](=[O:40])[NH:27][C:28]3[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[CH:32][C:29]=3[C:30]=2[N:31]=1>O1CCOCC1>[NH2:12][CH2:11][CH2:10][CH2:9][C:6]1[CH:5]=[C:4]([NH:20][C:21]2[N:22]=[CH:23][C:24]3[CH2:25][C:26](=[O:40])[NH:27][C:28]4[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[CH:32][C:29]=4[C:30]=3[N:31]=2)[C:3]([CH3:2])=[N:8][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68222737tert-butyl[3-(6-methyl-5-{[6-oxo-9-(trifluoromethyl)-6,7-dihydro-5H-pyrimido[5,4-d][1]benzazepin-2-yl]amino}pyridin-3-yl)propyl]carbamate

Product 1

HCID 594050242-{[5-(3-aminopropyl)-2-methylpyridin-3-yl]amino}-9-(trifluoromethyl)-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-oneYield 112.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 4M solution of HCl in dioxane (20 mL) was added tert-butyl [3-(6-methyl-5-{[6-oxo-9-(trifluoromethyl)-6,7-dihydro-5H-pyrimido[5,4-d][1]benzazepin-2-yl]amino}pyridin-3-yl)propyl]carbamate (1.10 g, 2.04 mmol). The reaction mixture was allowed to stir at rt overnight and then concentrated to give 2-{[5-(3-aminopropyl)-2-methylpyridin-3-yl]amino}-9-(trifluoromethyl)-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one (1.35 g, 2.30 mmol, >99%) as a brown solid. LCMS (FA): Rt=0.55 min, m/z=443.0 (M+H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-61d52717ba624e6cbf984eedec6e59d9
Source dataset
uspto-grants-2012_09
Patent number
US08268992B2

Reaction notes

Loading…