Hydrochloric Acid → HCID 58476555, compound

HRID 1672199Notes

Reaction equation

HRID 1672199 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]2[C:6]3[N:15]=[C:14]([NH:16][C:17]4[CH:18]=[CH:19][C:20]([NH:23]C(=O)C(C)(C)C)=[N:21][CH:22]=4)[N:13]=[CH:12][C:7]=3[CH2:8][C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1.Cl.C([O-])([O-])=O.[K+].[K+]>C1COCC1.CO.O>[NH2:23][C:20]1[N:21]=[CH:22][C:17]([NH:16][C:14]2[N:13]=[CH:12][C:7]3[CH2:8][C:9](=[O:11])[NH:10][C:4]4[CH:3]=[C:2]([Cl:1])[CH:31]=[CH:30][C:5]=4[C:6]=3[N:15]=2)=[CH:18][CH:19]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 59405011HCID 59405011, compound

Product 1

HCID 58476555HCID 58476555, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-{5-[(9-chloro-6-oxo-6,7-dihydro-5H-pyrimido[5,4-d][1]benzazepin-2-yl)amino]pyridin-2-yl}-2,2-dimethylpropanamide (0.220 g, 0.38 mmol) in THF (3 mL) and MeOH (4 mL) at rt was added 6M HCl in water (5 mL). The solution was allowed to stir at 100° C. for 22 h. The organic solvents were allowed to boil off and the aqueous mixture was allowed to cool to rt. Solid K2CO3 was added and the mixture was filtered. The resulting solid was collected and purified by column chromatography to give 2-[(6-aminopyridin-3-yl)amino]-9-chloro-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one (0.095 g, 71%).

Workup

  1. temperatureto cool to rt
  2. filtrationthe mixture was filtered
  3. customThe resulting solid was collected
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-fdd1935f7cc0457b892db3193c7ba791
Source dataset
uspto-grants-2011_08
Patent number
US07998952B2

Reaction notes

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