Trifluoroacetic acid → HCID 10515827, compound

HRID 2308214Notes

Reaction equation

HRID 2308214 reaction equation
C[CH2:2][N:3]([CH2:6][CH3:7])[CH2:4][CH3:5].[C:8]1([S:14](Cl)(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[N:18]#[C:19]N.C(O)(C(F)(F)F)=O.BrC#[N:30]>C(Cl)Cl.CCOC(C)=O>[C:2]([N:3]1[CH2:6][CH2:7][CH:5]([CH2:19][NH:18][S:14]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)(=[O:16])=[O:15])[CH2:4]1)#[N:30]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 9864CyanamideHCID 10476Cyanogen Bromide

Product 1

HCID 10515827HCID 10515827, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following general procedure 11, to a stirred solution of the amine (30) (109 mg, 1 equiv.) and Et3N (130 uL, 1.7 equiv.) in CH2Cl2 (7 mL) was added benzenesulfonyl chloride (97 uL, 1.4 equiv.). The resultant mixture was stirred at rt for 16 h. 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 (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 purified by flash chromatography (50% EtOAc in hexane) to afford the desired N-[(1-cyano-3-pyrrolidinyl)methyl]benzenesulfonamide (31).

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 (50% EtOAc in hexane)
  6. customto afford the
  7. customThe crude material was purified by flash chromatography (50% EtOAc in hexane)

Sources & evidence

ORD record
ord-1811602d5fb0464ab4aeb150f50b7844
Source dataset
uspto-grants-2004_12
Patent number
US06835727B2

Reaction notes

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