Hydrochloric Acid → (R)-7-[3-amino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid (2-dimethylamino-ethyl)-amide dihydrochloride

HRID 221489Notes

Reaction equation

HRID 221489 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:33][C:34]1[CH:39]=[C:38]([F:40])[C:37]([F:41])=[CH:36][C:35]=1[F:42])[CH2:9][C:10]([N:12]1[CH2:17][CH2:16][N:15]2[C:18]([C:29]([F:32])([F:31])[F:30])=[N:19][C:20]([C:21](=[O:28])[NH:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])=[C:14]2[CH2:13]1)=[O:11])(C)(C)C.[ClH:44]>C(OCC)(=O)C>[ClH:44].[ClH:44].[CH3:27][N:25]([CH3:26])[CH2:24][CH2:23][NH:22][C:21]([C:20]1[N:19]=[C:18]([C:29]([F:30])([F:31])[F:32])[N:15]2[CH2:16][CH2:17][N:12]([C:10](=[O:11])[CH2:9][C@H:8]([NH2:7])[CH2:33][C:34]3[CH:39]=[C:38]([F:40])[C:37]([F:41])=[CH:36][C:35]=3[F:42])[CH2:13][C:14]=12)=[O:28]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57518463HCID 57518463, compound

Product 1

HCID 86646921(R)-7-[3-amino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid (2-dimethylamino-ethyl)-amide dihydrochlorideYield 63%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

(R)-[3-[1-(2-Dimethylamino-ethylcarbamoyl)-3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazin-7-yl]-3-oxo-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic acid tert-butyl ester 29a (0.10 g, 0.16 mmol) was dissolved in 2 mL of ethyl acetate under stirring. A solution of 2.4 N hydrochloric acid in 6 mL of ethyl acetate was then added to the above solution. The reaction mixture was reacted at room temperature for 4 hours and monitored by thin layer chromatography until the disappearance of the starting materials. The reaction mixture was concentrated under reduced pressure, and 5 mL of ethyl acetate was added to the residue and filtered. The resulting white solid was rinsed with ethyl acetate to obtain the title compound (R)-7-[3-amino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid (2-dimethylamino-ethyl)-amide dihydrochloride 29(80 mg, yield 63%) as a white solid.

Workup

  1. customThe reaction mixture was reacted at room temperature for 4 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and 5 mL of ethyl acetate
  3. additionwas added to the residue
  4. filtrationfiltered
  5. washThe resulting white solid was rinsed with ethyl acetate

Sources & evidence

ORD record
ord-ce3a837e3583426180f9466c46ce2811
Source dataset
uspto-grants-2012_06
Patent number
US08207161B2

Reaction notes

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