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 1672197Notes

Reaction equation

HRID 1672197 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.[C:22]([O:26][C:27](=[O:43])[NH:28][CH2:29][CH2:30][CH2:31][C:32]1[CH:33]=[N:34][C:35]([CH3:42])=[C:36]([NH:38][C:39]([NH2:41])=[NH:40])[CH:37]=1)([CH3:25])([CH3:24])[CH3:23].C(=O)([O-])[O-].[K+].[K+]>CCO.O.CCOC(C)=O>[C:22]([O:26][C:27](=[O:43])[NH:28][CH2:29][CH2:30][CH2:31][C:32]1[CH:33]=[N:34][C:35]([CH3:42])=[C:36]([NH:38][C:39]2[N:41]=[CH:4][C:5]3[CH2:6][C:7](=[O:21])[NH:8][C:9]4[CH:16]=[C:15]([C:17]([F:20])([F:18])[F:19])[CH:14]=[CH:13][C:10]=4[C:11]=3[N:40]=2)[CH:37]=1)([CH3:24])([CH3:25])[CH3:23]

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-cbbe8eb9bf6c4960a7e3925d3b511c09
Source dataset
uspto-grants-2011_08
Patent number
US07998952B2

Reaction notes

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