Trifluoroacetic acid → HCID 22601268, compound

HRID 2308222Notes

Reaction equation

HRID 2308222 reaction equation
CC[N:3]([CH2:6][CH3:7])CC.[CH:8]1[C:16]2[C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[O:13][C:12]=2[CH:11]=[CH:10][C:9]=1[S:21](Cl)(=[O:23])=[O:22].[N:25]#[C:26][NH2:27].[C:28](O)(C(F)(F)F)=O.BrC#N>C(Cl)Cl.CCOC(C)=O>[C:26]([N:27]1[CH2:7][CH:6]([NH:3][S:21]([C:9]2[CH:10]=[CH:11][C:12]3[O:13][C:14]4[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=4[C:16]=3[CH:8]=2)(=[O:23])=[O:22])[CH2:28]1)#[N:25]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 9864CyanamideHCID 10476Cyanogen BromideHCID 27580308-Oxatricyclo(7.4.0.0,2,7)trideca-1(9),2(7),3,5,10,12-hexaene-4-sulfonyl chloride

Product 1

HCID 22601268HCID 22601268, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following general procedure 11, to a stirred solution of the amine (56) (256 mg, 1 equiv.) and Et3N (0.31 mL, 1.5 equiv.) in CH2Cl2 (5 mL) was added dibenzo[b,d]furan-2-sulfonyl chloride (356 mg, 0.9 equiv.). The resultant mixture was stirred at rt for 30 min. 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: 20% EtOAc in hexane to 50% 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 washed with ether to afford the desired yellow solid N-(1-cyano-3-azetidinyl)dibenzo[b,d]furan-2-sulfonamide (58).

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: 20% EtOAc in hexane to 50% EtOAc in hexane)
  6. customto afford the
  7. washThe crude material was washed with ether

Sources & evidence

ORD record
ord-d787bfcb223544cf9440798a79ebb0be
Source dataset
uspto-grants-2004_12
Patent number
US06835727B2

Reaction notes

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