Triethylamine → HCID 58824203, compound

HRID 1786581Notes

Reaction equation

HRID 1786581 reaction equation
[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][C:4]([O:7][CH2:8][C:9]2[CH:10]=[C:11]([S:15]([NH2:18])(=[O:17])=[O:16])[O:12][C:13]=2[CH3:14])=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:32](Cl)(=[O:36])[CH2:33][CH2:34][CH3:35]>ClCCl.CN(C)C1C=CN=CC=1>[C:32]([NH:18][S:15]([C:11]1[O:12][C:13]([CH3:14])=[C:9]([CH2:8][O:7][C:4]2[CH:3]=[CH:2][C:1]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:6][CH:5]=2)[CH:10]=1)(=[O:17])=[O:16])(=[O:36])[CH2:33][CH2:34][CH3:35]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 58824168HCID 58824168, compound

Product 1

HCID 58824203HCID 58824203, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-(biphenyl-4-yloxymethyl)-5-methyl-furan-2-sulphonic acid amide (45) (50 mg, 0.146 mmoles) in dichloromethane (5.0 ml) was added triethylamine (26 μl, 0.189 mmoles), dimethyl-pyridin-4-yl-amine (1 mg) and butyryl chloride (19 μl, 0.184 mmoles). After stirring for 16 hours at room temperature the reaction mixture was concentrated in-vacuo, and the residue was purified by HPLC to give compound 61 as an off-white solid (48 mg). LC/MS System C: Rt=3.82 mins, m/z (ES−)=412 (M−H) for C22H23NO5S).

Workup

  1. concentrationwas concentrated in-vacuo
  2. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-02dc82f64f374c8c91b15f796bec0e0c
Source dataset
uspto-grants-2009_03
Patent number
US07507754B2

Reaction notes

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