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 1892186Notes

Reaction equation

HRID 1892186 reaction equation
Cl.C(OC(=O)[NH:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[N:14][C:15]([CH3:39])=[C:16]([NH:18][C:19]2[N:20]=[CH:21][C:22]3[CH2:23][C:24](=[O:38])[NH:25][C:26]4[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][C:27]=4[C:28]=3[N:29]=2)[CH:17]=1)(C)(C)C>O1CCOCC1>[NH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[C:16]([NH:18][C:19]2[N:20]=[CH:21][C:22]3[CH2:23][C:24](=[O:38])[NH:25][C:26]4[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][C:27]=4[C:28]=3[N:29]=2)[C:15]([CH3:39])=[N:14][CH:13]=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-e9728b6b34ad474fa9a349931bac5804
Source dataset
uspto-grants-2013_08
Patent number
US08507667B2

Reaction notes

Loading…