Triethylamine → HCID 67138505, compound

HRID 1591995Notes

Reaction equation

HRID 1591995 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:4]=1[CH2:5][N:6]1[S:10](=[O:12])(=[O:11])[N:9]([CH2:13][C:14]2[S:18][C:17]([C:19](O)=[O:20])=[CH:16][CH:15]=2)[CH2:8][C:7]1=[O:22].O=S(Cl)Cl.[CH3:33][NH:34][CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.C(Cl)Cl>[CH3:33][N:34]([CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:19]([C:17]1[S:18][C:14]([CH2:13][N:9]2[CH2:8][C:7](=[O:22])[N:6]([CH2:5][C:4]3[CH:23]=[CH:24][C:25]([O:27][CH3:28])=[CH:26][C:3]=3[O:2][CH3:1])[S:10]2(=[O:12])=[O:11])=[CH:15][CH:16]=1)=[O:20]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11503N-MethylbenzeneethanamineHCID 24386Thionyl ChlorideHCID 67139805HCID 67139805, compound

Product 1

HCID 67138505HCID 67138505, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of the title D compound, 5-[5-(2,4-dimethoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]-thiophene-2-carboxylic acid (220 mg, 0.52 mmol) in toluene (10 mL) is treated with SOCl2 (3 mL) and the mixture is heated at 80° C. for 1 h. The volatiles are evaporated and the residue is dissolved in toluene. The solvent is evaporated again and the residue is dissolved in CH2Cl2(10 mL). A mixture of N-methylphenethylamine (35 mg, 0.25 mmol) and triethylamine (39 mg, 38.7 mmol) in CH2Cl2 (1 mL) is added and the mixture is stirred for 16 h. The solvent is evaporated and the residue is chromatographed over silica gel using 0-100% EtOAc in hexane as the eluent to afford 5-[5-(2,4-dimethoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]-thiophene-2-carboxylic acid methyl-phenethyl-amide as a clear oil: [M+1]+=544.

Workup

  1. customThe volatiles are evaporated
  2. dissolutionthe residue is dissolved in toluene
  3. customThe solvent is evaporated again
  4. dissolutionthe residue is dissolved in CH2Cl2(10 mL)
  5. additionis added
  6. customThe solvent is evaporated
  7. customthe residue is chromatographed over silica gel using 0-100% EtOAc in hexane as the eluent

Sources & evidence

ORD record
ord-6470d362be734a2d9139f89b0d868856
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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