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 1895600Notes

Reaction equation

HRID 1895600 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-cd218266ffd34d35adefe3e185fe21f3
Source dataset
uspto-grants-2013_08
Patent number
US08513411B2

Reaction notes

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