Water → HCID 59405030, compound

HRID 1672192Notes

Reaction equation

HRID 1672192 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6](=O)/[C:7](=[CH:12]/N(C)C)/[CH2:8][C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1.[CH3:19][C:20]1[C:25]([NH:26][C:27]([NH2:29])=[NH:28])=[CH:24][CH:23]=[C:22]([NH:30][CH:31]2[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]2)[N:21]=1.C(=O)([O-])[O-].[K+].[K+].O>CCO>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6]3[N:29]=[C:27]([NH:26][C:25]4[C:20]([CH3:19])=[N:21][C:22]([NH:30][CH:31]5[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]5)=[CH:23][CH:24]=4)[N:28]=[CH:12][C:7]=3[CH2:8][C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 13133569HCID 13133569, compoundHCID 178433122HCID 178433122, compound

Product 1

HCID 59405030HCID 59405030, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To (4E)-8-chloro-4-[(dimethylamino)methylene]-3,4-dihydro-1H-1-benzazepine-2,5-dione (3.25 g. 12.3 mmol) in EtOH (50 mL) were added N-{2-methyl-6-[(1-methylpiperidin-4-yl)amino]pyridin-3-yl}guanidine *xHCl (6.5 g, 14 mmol) and potassium carbonate (13.6 g, 98.3 mmol). The reaction mixture was allowed to stir for 2 days at 70° C. and then allowed to cool to room temperature. The solids were filtered and the filtrate was concentrated to give a thick red oil. Water was added to the residue and the aqueous solution was extracted with EtOAc. The organic solutions were combined, dried, filtered and concentrated to give 9-chloro-2-({2-methyl-6-[(1-methylpiperidin-4-yl)amino]pyridin-3-yl}amino)-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one (5,3 g, 93%).

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe solids were filtered
  3. concentrationthe filtrate was concentrated
  4. customto give a thick red oil
  5. extractionthe aqueous solution was extracted with EtOAc
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c9a2db55d34e4f4bbdb2bcfde9a6021a
Source dataset
uspto-grants-2011_08
Patent number
US07998952B2

Reaction notes

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