Ammonia → HCID 178428444, compound

HRID 1932415Notes

Reaction equation

HRID 1932415 reaction equation
S(=O)(=O)(O)O.[CH2:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][N:7]1[C:16]1[N:17]=[C:18](N)[CH:19]=[C:20]2[C:24]([CH3:25])=[C:23]([CH3:26])[N:22]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=3)[C:21]=12.N([O-])=[O:37].[Na+].N>O>[CH2:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][N:7]1[C:16]1[N:17]=[C:18]([OH:37])[CH:19]=[C:20]2[C:24]([CH3:25])=[C:23]([CH3:26])[N:22]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=3)[C:21]=12

Participants

6

Reactant 4

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 23668193Sodium NitriteHCID 67142088HCID 67142088, compound

Product 1

HCID 178428444HCID 178428444, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

The compound prepared in Example 847 was treated with a saturated sodium bicarbonate solution to obtain 7-(3,4-dihydro-1H-isoquinolin-2-yl)-1-(3-fluorobenzyl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-5-amine. Concentrated sulfuric acid (1 ml) and water (5 ml) were added to 7-(3,4-dihydro-1H-isoquinolin-2-yl)-1-(3-fluorobenzyl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-5-amine (50 mg, 0.13 mmol) and then sodium nitrite (43.1 mg, 0.63 mmol) was added thereto. The reaction mixture was stirred for 5 minutes at 100° C. under heating and then excess ammonia solution was added thereto. The reaction mixture was stirred for 2 minutes under heating at the same temperature and then filtered to discard insoluble materials. A potassium hydroxide solution was added to the reaction mixture, which was then filtered to discard insoluble materials. The reaction mixture was extracted with ethyl acetate. The organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure to give 28.4 mg of the titled compound as a pale yellow solid.

Workup

  1. temperatureunder heating
  2. stirringThe reaction mixture was stirred for 2 minutes
  3. temperatureunder heating at the same temperature
  4. filtrationfiltered
  5. additionA potassium hydroxide solution was added to the reaction mixture, which
  6. filtrationwas then filtered
  7. extractionThe reaction mixture was extracted with ethyl acetate
  8. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a89787f3a143432daf3cedab6691d1ce
Source dataset
uspto-grants-2012_05
Patent number
US08188114B2

Reaction notes

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