Hydrochloric Acid → HCID 66734088, compound

HRID 1929721Notes

Reaction equation

HRID 1929721 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH2:18][CH3:19])=[N:15][C:16]([Cl:17])=[C:10]2[CH:9]1[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=1)=O)(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[Cl:17][C:16]1[N:15]=[C:14]([CH2:18][CH3:19])[N:11]2[CH2:12][CH2:13][NH:8][CH:9]([CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:30])([F:29])[F:31])=[CH:24][CH:23]=3)[C:10]=12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66733744HCID 66733744, compound

Product 1

HCID 66734088HCID 66734088, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To an ice-cooled solution of 1-chloro-3-ethyl-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester (226 mg; 0.494 mmol) in DCM (5 ml) was added 4N HCl in dioxane (2.5 ml; 10 mmol; 20 eq.). The resulting suspension was further stirred at 0° C. for 10 min., and at rt for 2 h. The volatiles were removed under vacuum and the resulting pale yellow chlorhydrate salt (240 mg) was purified by preparative HPLC in basic conditions leading to the pure product 1-chloro-3-ethyl-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine (89.6 mg; 51%). LC-MS: tR=0.77 min.; [M+H]+=358.36 g/mol.

Workup

  1. waitat rt for 2 h
  2. customThe volatiles were removed under vacuum
  3. customthe resulting pale yellow chlorhydrate salt (240 mg) was purified by preparative HPLC in basic conditions

Sources & evidence

ORD record
ord-d671ca9eeadf488d80f171573b4b3728
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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