Ammonia → HCID 59852752, compound

HRID 2373929Notes

Reaction equation

HRID 2373929 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([F:29])=[C:11]([C:15]2[N:16]=[C:17]([CH:25]3[CH2:28][CH2:27][CH2:26]3)[N:18]3[CH:23]=[CH:22][N:21]=[C:20](Cl)[C:19]=23)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:30]>C(Cl)Cl.CC(O)C>[NH2:30][C:20]1[C:19]2[N:18]([C:17]([CH:25]3[CH2:28][CH2:27][CH2:26]3)=[N:16][C:15]=2[C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:10]=2[F:29])[CH:23]=[CH:22][N:21]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 59852783HCID 59852783, compound

Product 1

HCID 59852752HCID 59852752, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
125 °C

Procedure

1-(3-Benzyloxy-2-fluoro-phenyl)-8-chloro-3-cyclobutyl-imidazo[1,5-a]pyrazine (500 mg, 1.2 mmole) in methylene chloride was placed in a Parr pressure reactor, cooled in ice salt bath and charged with a saturated solution of NH3 in 2-propanol (10 mL). The pressure reactor was heated at 125° C. overnight. The reaction was cooled to room temperature and the crude reaction mixture was evaporated and triturated with methylene chloride and filtered. The filtrate was evaporated to dryness and purified by silica-gel column chromatography [eluant CH2Cl2:hexane (70:30)] to afford the title compound (350 mg, 75%); FAB-MS: m/z 388.9 (M+H)+.

Workup

  1. temperaturecooled in ice salt bath
  2. temperatureThe reaction was cooled to room temperature
  3. customthe crude reaction mixture
  4. customwas evaporated
  5. customtriturated with methylene chloride
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. custompurified by silica-gel column chromatography [eluant CH2Cl2:hexane (70:30)]

Sources & evidence

ORD record
ord-15a0609c553c4c69b2212ebf8d2371dd
Source dataset
uspto-grants-2008_12
Patent number
US07459554B2

Reaction notes

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