Ethylmorpholine → 5-(3,5-dichlorophenylthio)-4-isopropyl-2-methyl-1-[(4-pyridyl)methyl]-1H-pyrrole

HRID 1582657Notes

Reaction equation

HRID 1582657 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[C:13]([CH3:22])=[C:12](C(O)=O)[C:11]=2[CH:26]([CH3:28])[CH3:27])[CH:5]=[C:6]([Cl:8])[CH:7]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.COC1C=C(OC)C=C(OC)C=1CN.C(N1CCOCC1)C>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[C:13]([CH3:22])=[CH:12][C:11]=2[CH:26]([CH3:28])[CH3:27])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 101378285-(3,5-Dichlorophenylthio)-2-methyl-4-isopropyl-1-[(4-pyridyl)methyl]-1H-pyrrole-3-carboxylic acidHCID 162119141-(2,4,6-Trimethoxyphenyl)methanamine--hydrogen chloride (1/1)

Product 1

HCID 227183995-(3,5-dichlorophenylthio)-4-isopropyl-2-methyl-1-[(4-pyridyl)methyl]-1H-pyrroleYield 20.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 160 mg of 5-(3,5-Dichlorophenylthio)-2-methyl-4-isopropyl-1-[(4-pyridyl)methyl]-1H-pyrrole-3-carboxylic acid in 10 ml of dichloromethane were added 60 mg of EDAC, 40 mg of HOBt, 68 mg of 2,4,6-trimethoxybenzylamine hydrochloride and 0.11 ml of N-ethyl morpholine. The reaction mixture was stirred at room temperature for 18 h. The reaction was quenched with saturated sodium bicarbonate solution and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulphate, filtered and evaporated. The residue was purified by flash chromatography on silica gel using petrol/ethyl acetate (1:4 then 1:2) then ethyl acetate for the elution to give 29 mg of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-methyl-1-[(4-pyridyl)methyl]-1H-pyrrole as an oil, mass spectrum (ESI) m/z 391 [M+H]+ and 114 mg of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-methyl-1-[(4-pyridyl)methyl]-1H-pyrrole-3-N-[(2,4,6-trimethoxy)benzyl]-carboxamide as an oil, mass spectrum (ESI) m/z 614 [M+H]+.

Workup

  1. customThe reaction was quenched with saturated sodium bicarbonate solution
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel
  7. wash1:2) then ethyl acetate for the elution

Sources & evidence

ORD record
ord-b84c9dec45e348fbb5542d5f995327c4
Source dataset
uspto-grants-2004_05
Patent number
US06737429B2

Reaction notes

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