Hydrochloric Acid → 8-Butyl-7-(3-(imidazol-5-yl)-1-oxopropyl)-2-(2-methoxyphenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine

HRID 901118

Reaction equation

HRID 901118 reaction equation
[CH2:1]([CH:5]1[N:10]([C:11](=[O:26])[CH2:12][CH2:13][C:14]2[NH:18][C:17](C(OC(C)(C)C)=O)=[N:16][CH:15]=2)[CH2:9][CH2:8][N:7]2[CH:27]=[C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36][CH3:37])[N:29]=[C:6]12)[CH2:2][CH2:3][CH3:4].Cl>CO>[CH2:1]([CH:5]1[N:10]([C:11](=[O:26])[CH2:12][CH2:13][C:14]2[NH:18][CH:17]=[N:16][CH:15]=2)[CH2:9][CH2:8][N:7]2[CH:27]=[C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36][CH3:37])[N:29]=[C:6]12)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22928230HCID 22928230, compound

Product 1

HCID 229282328-Butyl-7-(3-(imidazol-5-yl)-1-oxopropyl)-2-(2-methoxyphenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazineYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Step 1.g. (450 mg, 0.89 mmol) was dissolved in MeOH (5 ml) and 4N HCl was added and the reaction was stirred at room temperature for about ½ hour. Solvents were removed under reduced pressure to yield 420 mg of crude product. Part of the crude (100 mg) was purified by preparative HPLC on a RAININ™ C18 column (Varian Analytical, Walnut Creek, Calif.) using a gradient of 10-30% CH3CN/aq. HCl (pH=2.0) over 45 minutes with UV detection at 254 nm. Product fractions were concentrated to about ½ volume and lyophilized to yield pure product (47 mg, 47%) as the di-hydrochloride. Mass spec. 508.2 MH−.

Workup

  1. customSolvents were removed under reduced pressure
  2. customto yield 420 mg of crude product
  3. customPart of the crude (100 mg) was purified by preparative HPLC on a RAININ™ C18 column (Varian Analytical, Walnut Creek, Calif.)
  4. waitHCl (pH=2.0) over 45 minutes with UV detection at 254 nm
  5. concentrationProduct fractions were concentrated to about ½ volume

Sources & evidence

ORD record
ord-d4ca6bf72e184cdfaa72d2489d5d26da
Source dataset
uspto-grants-2008_04
Patent number
US07361656B2

Linked notes

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