Ethanol hydrochloride → HCID 136335109, compound

HRID 2376188Notes

Reaction equation

HRID 2376188 reaction equation
[F:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[CH2:4][N:5]1[CH2:9][CH2:8][C@@H:7]([NH:10][C:11]2[N:12]=[CH:13][C:14](/[CH:17]=[CH:18]/[C:19]([NH:21][O:22]C3CCCCO3)=[O:20])=[N:15][CH:16]=2)[CH2:6]1.[ClH:33].C(O)C>C(OCC)(=O)C>[ClH:33].[ClH:33].[F:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[CH2:4][N:5]1[CH2:9][CH2:8][C@@H:7]([NH:10][C:11]2[N:12]=[CH:13][C:14](/[CH:17]=[CH:18]/[C:19]([NH:21][OH:22])=[O:20])=[N:15][CH:16]=2)[CH2:6]1

Participants

4

Reactant 2

HCID 21887872Ethanol hydrochlorideHCID 86603826HCID 86603826, compound

Product 1

HCID 136335109HCID 136335109, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (2E)-3-(5-{[(3R)-1-(2-fluorobenzyl)-3-pyrrolidinyl]amino}-2-pyrazinyl)-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide (600 mg) and 2N HCl/Ethanol (13.6 ml, 20 eq) was stirred at room temperature for 2 hours. After then, ethyl acetate (10 ml) and IPE (50 ml) was added and stirred. Precipitate was filtered, washed with IPE, and dried under reduced pressure to give 486 mg (83%) of (2E)-3-(5-{[(3R)-1-(2-fluorobenzyl)-3-pyrrolidinyl]amino}-2-pyrazinyl)-N-hydroxyacrylamide dihydrochloride as a powder.

Workup

  1. stirringstirred
  2. filtrationPrecipitate was filtered
  3. washwashed with IPE
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-753f2d9679c74eaa8dab06fb157f9c10
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

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