Hydrochloric Acid → 7-[(3R)-3-Amino-4-(3,4-difluorophenyl)butanoyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine, dihydrochloride

HRID 47592Notes

Reaction equation

HRID 47592 reaction equation
CC(C)(OC([NH:7][C@H:8]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[C:24]([F:29])[CH:23]=1)[CH2:9][C:10]([N:12]1[CH2:17][CH2:16][N:15]2[CH:18]=[CH:19][N:20]=[C:14]2[CH2:13]1)=[O:11])=O)C.[ClH:31]>CO>[ClH:31].[ClH:31].[NH2:7][C@H:8]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[C:24]([F:29])[CH:23]=1)[CH2:9][C:10]([N:12]1[CH2:17][CH2:16][N:15]2[CH:18]=[CH:19][N:20]=[C:14]2[CH2:13]1)=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 670585127-[(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(3,4-difluorophenyl)butanoyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine

Product 1

HCID 1317243627-[(3R)-3-Amino-4-(3,4-difluorophenyl)butanoyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine, dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared from 7-[(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(3,4-difluorophenyl)butanoyl]-5,6,7,8-tetrahydroimidazo[1,2-α]pyrazine (72 mg, 0.171 mmol, from Step C), in 1.5 mL of methanol saturated with hydrogen chloride, using a procedure analogous to that described in Example 1, Step D. Concentration gave 66 mg of the title compound as a foamy solid. 1H NMR (500 MHz, CD3OD) δ 2.96-3.13 (m, 4H), 3.93 (m, 1H), 4.13 (m, 2H), 4.26-4.38 (m, 2H), 4.26-4.38 (m, 2H), 4.90-5.04 (m, 2H), 7.19-7.36 (m, 3H), 7.58 (m, 1H). ESI-MS 321 (M+1).

Workup

  1. concentrationConcentration

Sources & evidence

ORD record
ord-5def85691a254633afa89cc249cfbb4e
Source dataset
uspto-grants-2004_03
Patent number
US06699871B2

Reaction notes

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