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Sodium Hydroxide → HCID 73386771, compound

HRID 1480768
Notes
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Reaction equation

HRID 1480768 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][CH:14]=O)=[C:9]([O:16][CH3:17])[CH:8]=2)=[CH:5][N:4]=[C:3]1[CH3:18].[H-].[Na+].[CH3:21][N:22]1[CH:26]=[C:25]([C:27]2[C:32]3[N:33]=C(S(C)(=O)=O)[N:35]=[CH:36][C:31]=3[CH:30]=[CH:29][N:28]=2)[CH:24]=[N:23]1.[OH-].[Na+]>C1COCC1.CO>[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:35]=[CH:36][C:31]4[CH:30]=[CH:29][N:28]=[C:27]([C:25]5[CH:24]=[N:23][N:22]([CH3:21])[CH:26]=5)[C:32]=4[N:33]=3)=[C:9]([O:16][CH3:17])[CH:8]=2)=[CH:5][N:4]=[C:3]1[CH3:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 89996010HCID 89996010, compoundHCID 89996058HCID 89996058, compound

Product 1

HCID 73386771HCID 73386771, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-(4-(1,2-dimethyl-1H-imidazol-5-yl)-2-methoxyphenyl)formamide (Preparation 55, 37 mg, 0.151 mmol) in THF (1 mL) was treated with sodium hydride (10 mg, 0.250 mmol) at 0° C. After stirring for 20 minutes at room temperature, the mixture was cooled to 0° C. and 8-(1-methyl-1H-pyrazol-4-yl)-2-(methylsulfonyl)pyrido[3,4-d]pyrimidine (Preparation 35, 50 mg, 0.173 mmol) was added. The reaction was allowed to reach room temperature and stirred for 18 hours. Aqueous NaOH (2M, 0.5 mL) and MeOH (0.5 mL) were added and the resulting mixture stirred at room temperature for 1 hour. The volatiles were removed under reduced pressure and the residue was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with water, brine, dried and evaporated. The residue was purified by silica gel column chromatography eluting with 0 to 10% MeOH in EtOAc to give the title compound (9 mg, 14%).

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. customto reach room temperature
  3. stirringstirred for 18 hours
  4. stirringthe resulting mixture stirred at room temperature for 1 hour
  5. customThe volatiles were removed under reduced pressure
  6. customthe residue was partitioned between EtOAc and water
  7. extractionThe aqueous layer was extracted with EtOAc
  8. washthe combined organic layers were washed with water, brine
  9. customdried
  10. customevaporated
  11. customThe residue was purified by silica gel column chromatography
  12. washeluting with 0 to 10% MeOH in EtOAc

Sources & evidence

ORD record
ord-3ebbb98288fb495c9b6d4ea1ff1bda8d
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09409907B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes