1,1'-Carbonyldiimidazole → HCID 68106726, compound

HRID 2409601Notes

Reaction equation

HRID 2409601 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([O:32][CH3:33])[C:30]=1[CH3:31])[C:6]([N:8]([CH2:18][C:19]1[S:20][C:21]([CH3:27])=[C:22]([C:24](O)=[O:25])[N:23]=1)[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7].C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:46][N:47]([CH3:52])[S:48]([NH2:51])(=[O:50])=[O:49].C1CCN2C(=NCCC2)CC1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([O:32][CH3:33])[C:30]=1[CH3:31])[C:6]([N:8]([CH2:18][C:19]1[S:20][C:21]([CH3:27])=[C:22]([C:24]([NH:51][S:48]([N:47]([CH3:52])[CH3:46])(=[O:50])=[O:49])=[O:25])[N:23]=1)[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7]

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 134472N,N-DimethylsulfamideHCID 68106800HCID 68106800, compound

Product 1

HCID 68106726HCID 68106726, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

2-{[(3,5-Dimethoxy-4-methylbenzoyl)(3-phenylpropyl)amino]methyl}-5-methyl-1,3-thiazole-4-carboxylic acid (150 mg) and CDI (78 mg) was added to anhydrous THF (5 mL), followed by heating at 60° C. for about 1 hour. To the reaction mixture were added N,N-dimethylsulfamide (60 mg) and DBU (73 mg) under ice-cooling, respectively, followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and neutralized by the addition of an appropriate amount of purified water and 1 M hydrochloric acid, and then extracted from chloroform. The obtained organic layer was dried over MgSO4, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1:2) to obtain 2-{[(3,5-dimethoxy-4-methylbenzoyl)(3-phenylpropyl)amino]methyl}-N-[(dimethylamino)sulfonyl]-5-methyl-1,3-thiazole-4-carboxamide (111 mg) as a white solid.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionneutralized by the addition of an appropriate amount of purified water and 1 M hydrochloric acid
  4. extractionextracted from chloroform
  5. dry with materialThe obtained organic layer was dried over MgSO4
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1:2)

Sources & evidence

ORD record
ord-8d8f76a6fe1a44d9a88cd0637a63f06b
Source dataset
uspto-grants-2014_08
Patent number
US08815920B2

Reaction notes

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