1,2-Dichloroethane → HCID 58393271, compound

HRID 469036Notes

Reaction equation

HRID 469036 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([NH:11][C:12]([C:14]2[CH:18]=[C:17]([CH2:19][N:20]([S:22]([C:25]3[C:30]([CH3:31])=[CH:29][C:28]([O:32][CH3:33])=[CH:27][C:26]=3[CH3:34])(=[O:24])=[O:23])[CH3:21])[O:16][CH:15]=2)=[O:13])[CH3:10])=[CH:5][CH:4]=1)=O.[NH:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1.CC(O)=O.ClCCCl>C(Cl)Cl>[CH3:33][O:32][C:28]1[CH:29]=[C:30]([CH3:31])[C:25]([S:22]([N:20]([CH2:19][C:17]2[O:16][CH:15]=[C:14]([C:12]([NH:11][CH:9]([C:6]3[CH:7]=[CH:8][C:3]([CH2:1][N:35]4[CH2:39][CH2:38][CH2:37][CH2:36]4)=[CH:4][CH:5]=3)[CH3:10])=[O:13])[CH:18]=2)[CH3:21])(=[O:24])=[O:23])=[C:26]([CH3:34])[CH:27]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 31268PyrrolidineHCID 58393017HCID 58393017, compound

Product 1

HCID 58393271HCID 58393271, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to general procedure BF using N-[1-(4-formylphenyl)ethyl]-5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxamide (39 mg, 0.08 mmol), pyrrolidine (6.8 mg, 0.1 mmol), AcOH (7 mg, 0.12 mmol), STAB (34 mg, 0.16 mmol) and DCE (1 mL). The reaction was diluted with DCM (1 mL) and washed with saturated aqueous NaHCO3 solution (5 mL). The organic phase was dried over Na2SO4 and the solvent removed in vacuo. The crude product was purified by FCC eluting with 2-10% MeOH in DCM to afford the title compound.

Workup

  1. customThe title compound was prepared
  2. washwashed with saturated aqueous NaHCO3 solution (5 mL)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customthe solvent removed in vacuo
  5. customThe crude product was purified by FCC
  6. washeluting with 2-10% MeOH in DCM

Sources & evidence

ORD record
ord-3340894ad41e426c9a654f8b28900436
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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