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Hydrochloric Acid → N-[(4'R)-2''-amino-2',2'-dimethyldispiro[cyclopropane-1,3'-chromene-4',4''-[1,3]oxazol]-6'-yl]-5-(difluoromethyl)pyrazine-2-carboxamide hydrochloride

HRID 594919
Notes
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Reaction equation

HRID 594919 reaction equation
[NH2:1][C:2]1[O:3][CH2:4][C@@:5]2([C:15]3[C:10](=[CH:11][CH:12]=[C:13]([NH:16][C:17]([C:19]4[CH:24]=[N:23][C:22]([CH:25]([F:27])[F:26])=[CH:21][N:20]=4)=[O:18])[CH:14]=3)[O:9][C:8]([CH3:29])([CH3:28])[C:7]32[CH2:31][CH2:30]3)[N:6]=1.[ClH:32].C(OCC)(=O)C>CO>[ClH:32].[NH2:1][C:2]1[O:3][CH2:4][C@@:5]2([C:15]3[C:10](=[CH:11][CH:12]=[C:13]([NH:16][C:17]([C:19]4[CH:24]=[N:23][C:22]([CH:25]([F:27])[F:26])=[CH:21][N:20]=4)=[O:18])[CH:14]=3)[O:9][C:8]([CH3:29])([CH3:28])[C:7]32[CH2:31][CH2:30]3)[N:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 86724318N-[(4'R)-2''-amino-2',2'-dimethyldispiro[cyclopropane-1,3'-chromene-4',4''-[1,3]oxazol]-6'-yl]-5-(difluoromethyl)pyrazine-2-carboxamide

Product 1

HCID 86724321N-[(4'R)-2''-amino-2',2'-dimethyldispiro[cyclopropane-1,3'-chromene-4',4''-[1,3]oxazol]-6'-yl]-5-(difluoromethyl)pyrazine-2-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[(4′R)-2″-amino-2′,2′-dimethyldispiro[cyclopropane-1,3′-chromene-4′,4″-[1,3]oxazol]-6′-yl]-5-(difluoromethyl)pyrazine-2-carboxamide (800 mg, 1.86 mmol) in MeOH (10 mL) was added 4M solution of hydrogen chloride in ethyl acetate (0.5 mL, 2 mmol) and the mixture was concentrated in vacuo. The residue was triturated with EtOH (10 mL), and the mixture was refluxed for 30 minutes and stirred at room temperature overnight. The precipitate was collected, washed with EtOH (2 mL), and dried under reduced pressure at 70° C. overnight to afford N-[(4′R)-2″-amino-2′,2′-dimethyldispiro[cyclopropane-1,3′-chromene-4′,4″-[1,3]oxazol]-6′-yl]-5-(difluoromethyl)pyrazine-2-carboxamide hydrochloride (449 mg) as a crystal.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe residue was triturated with EtOH (10 mL)
  3. temperaturethe mixture was refluxed for 30 minutes
  4. customThe precipitate was collected
  5. washwashed with EtOH (2 mL)
  6. customdried under reduced pressure at 70° C. overnight

Sources & evidence

ORD record
ord-aa073ff10f4a4991829ed58ac26778ed
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09242973B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes