Potassium Carbonate → 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

HRID 2387987Notes

Reaction equation

HRID 2387987 reaction equation
CN(/[CH:4]=[C:5]1/[CH2:6][C:7](=[O:21])[NH:8][C:9]2[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:10]=2[C:11]/1=O)C.[NH2:22][C:23]([NH:25][C:26]1[CH:27]=[C:28]([CH2:33][CH2:34][CH2:35][NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH:29]=[N:30][C:31]=1[CH3:32])=[NH:24].C(=O)([O-])[O-].[K+].[K+]>CCO.O.CCOC(C)=O>[CH3:32][C:31]1[N:30]=[CH:29][C:28]([CH2:33][CH2:34][CH2:35][NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[CH:27][C:26]=1[NH:25][C:23]1[N:22]=[CH:4][C:5]2[CH2:6][C:7](=[O:21])[NH:8][C:9]3[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:10]=3[C:11]=2[N:24]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 59405000(4Z)-4-[(dimethylamino)methylene]-8-(trifluoromethyl)-3,4-dihydro-1H-1-benzazepine-2,5-dioneHCID 178432741HCID 178432741, compound

Product 1

HCID 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]carbamateYield 111.8%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (4Z)-4-[(dimethylamino)methylene]-8-(trifluoromethyl)-3,4-dihydro-1H-1-benzazepine-2,5-dione (1.05 g, 3.51 mmol) and tert-butyl [3-(5-{[amino(imino)methyl]amino}-6-methylpyridin-3-yl)propyl]carbamate (1.62 g, 5.27 mmol) in EtOH (50 mL) was added potassium carbonate (2.91 g, 21.1 mmol). The reaction mixture was allowed to stir at 80° C. overnight. The reaction mixture was diluted with water (100 mL) and EtOAc (50 mL). The organic solution was separated and the aqueous solution was extracted with EtOAc (2×50 mL). The organic solutions were combined, washed with brine (100 mL), dried over MgSO4, filtered and concentrated to give 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 (2.13 g, >99%) as a dark brown solid. LCMS (FA): Rt=1.79 min, m/z=543.0 (M+H).

Workup

  1. customThe organic solution was separated
  2. extractionthe aqueous solution was extracted with EtOAc (2×50 mL)
  3. washwashed with brine (100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-38b6ebed172747b381368f7e8a156bb3
Source dataset
uspto-grants-2012_09
Patent number
US08268992B2

Reaction notes

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