Trifluoroacetic acid → HCID 9920989, compound

HRID 2308211Notes

Reaction equation

HRID 2308211 reaction equation
C[CH2:2][N:3]([CH2:6][CH3:7])[CH2:4][CH3:5].[C:8](Br)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[N:17]#[C:18]N.C(O)(C(F)(F)F)=O.BrC#[N:29]>C(Cl)Cl.CCOC(C)=O>[C:2]([N:3]1[CH2:6][CH2:7][CH2:5][CH:4]1[CH2:18][NH:17][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)#[N:29]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 9864CyanamideHCID 10476Cyanogen BromideHCID 12056Benzoyl bromide

Product 1

HCID 9920989HCID 9920989, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following general procedure 10, to a stirred solution of the amine (16) (200 mg, 1 equiv.) and Et3N (0.21 mL, 1.5 equiv.) in CH2Cl2 (5 mL) was added benzoyl bromide (0.13 mL, 1.1 equiv.). The resultant mixture was stirred at rt for 30 minutes. The mixture was then diluted with EtOAc and washed successively with 10% citric acid, H2O and brine. The organic extract was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution: 10% EtOAc in hexane to 33% EtOAc in hexane) to afford the desired coupled product. The N-Boc group of the coupled product was then converted to the cyanamide (N—CN) following general procedure 3 (i.e. successive treatment with TFA and BrCN). The crude material was purified by flash chromatography (gradient elution: 50% EtOAc in hexane to 67% EtOAc in hexane) to afford the desired N-[(1-cyano-2-pyrrolidinyl)methyl]benzamide (17).

Workup

  1. washwashed successively with 10% citric acid, H2O and brine
  2. extractionThe organic extract
  3. dry with materialwas dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (gradient elution: 10% EtOAc in hexane to 33% EtOAc in hexane)
  6. customto afford the
  7. customThe crude material was purified by flash chromatography (gradient elution: 50% EtOAc in hexane to 67% EtOAc in hexane)

Sources & evidence

ORD record
ord-1ab3cf5ba9c54b82b35ac654d4a9540e
Source dataset
uspto-grants-2004_12
Patent number
US06835727B2

Reaction notes

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