Hydrochloric Acid → (R)-1-{7-[3-amino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carbonyl}-piperidine-4-carboxylic acid amide hydrochloride

HRID 221442Notes

Reaction equation

HRID 221442 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:36][C:37]1[CH:42]=[C:41]([F:43])[C:40]([F:44])=[CH:39][C:38]=1[F:45])[CH2:9][C:10]([N:12]1[CH2:17][CH2:16][N:15]2[C:18]([C:32]([F:35])([F:34])[F:33])=[N:19][C:20]([C:21]([N:23]3[CH2:28][CH2:27][CH:26]([C:29](=[O:31])[NH2:30])[CH2:25][CH2:24]3)=[O:22])=[C:14]2[CH2:13]1)=[O:11])(C)(C)C.[ClH:47]>C(OCC)(=O)C>[ClH:47].[NH2:7][C@H:8]([CH2:36][C:37]1[CH:42]=[C:41]([F:43])[C:40]([F:44])=[CH:39][C:38]=1[F:45])[CH2:9][C:10]([N:12]1[CH2:17][CH2:16][N:15]2[C:18]([C:32]([F:35])([F:34])[F:33])=[N:19][C:20]([C:21]([N:23]3[CH2:28][CH2:27][CH:26]([C:29]([NH2:30])=[O:31])[CH2:25][CH2:24]3)=[O:22])=[C:14]2[CH2:13]1)=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57518415(R)-[3-[1-(4-carbamoyl-piperidine-1-carbonyl)-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

Product 1

HCID 44193938(R)-1-{7-[3-amino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carbonyl}-piperidine-4-carboxylic acid amide hydrochlorideYield 74%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

(R)-[3-[1-(4-Carbamoyl-piperidine-1-carbonyl)-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 7a (0.18 g, 0.27 mmol) and 2 mL of ethyl acetate were added into the reaction flask. A solution of 2.3 N hydrochloric acid in 6 mL of ethyl acetate was then added to the flask. The reaction mixture was reacted at room temperature for 3.5 hours and monitored by thin layer chromatography until the disappearance of the starting materials. The reaction mixture was concentrated under reduced pressure to obtain the title compound (R)-1-{7-[3-amino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carbonyl}-piperidine-4-carboxylic acid amide hydrochloride 7 (0.12 g, yield 74%) as a white solid.

Workup

  1. customThe reaction mixture was reacted at room temperature for 3.5 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7d37c9ab17924051986d43d9aa4722af
Source dataset
uspto-grants-2012_06
Patent number
US08207161B2

Reaction notes

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