1,1'-Carbonyldiimidazole → HCID 57901864, compound

HRID 1851555Notes

Reaction equation

HRID 1851555 reaction equation
[CH3:1][N:2]([S:22]([C:25]1[S:26][CH:27]=[CH:28][CH:29]=1)(=[O:24])=[O:23])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][C:14]([CH2:17][CH2:18][C:19](O)=[O:20])=[CH:15][N:16]=1)=[CH:8]2.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:42][S:43]([NH2:46])(=[O:45])=[O:44].C1CCN2C(=NCCC2)CC1>O1CCCC1>[CH3:42][S:43]([NH:46][C:19](=[O:20])[CH2:18][CH2:17][C:14]1[S:13][C:12]([C:9]2[NH:10][C:11]3[C:7]([CH:8]=2)=[CH:6][CH:5]=[CH:4][C:3]=3[N:2]([CH3:1])[S:22]([C:25]2[S:26][CH:27]=[CH:28][CH:29]=2)(=[O:23])=[O:24])=[N:16][CH:15]=1)(=[O:45])=[O:44]

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57901696HCID 57901696, compound

Product 1

HCID 57901864HCID 57901864, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(2-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazol-5-yl)propanoic acid (0.3.0 g), 1,1′-carbonylbis-1H-imidazole (0.27 g) and tetrahydrofuran (10 mL) was heated under reflux for 2 hr. The reaction mixture was cooled to room temperature, methanesulfonamide (0.32 g) and 1,8-diazabicyclo[5.4.0]-7-undecene (0.50 mL) were added, and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated and 10% aqueous citric acid solution was added. The resulting crystals were collected by filtration, washed with water and dried. The obtained crystals were subjected to silica gel column chromatography and the title compound (0.21 g, yield 60%) was obtained as yellow crystals from a fraction eluted with tetrahydrofuran-hexane (3:1, volume ratio). The crystals were recrystallized from ethyl acetate. melting point 217-218° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hr
  3. concentrationThe reaction mixture was concentrated
  4. addition10% aqueous citric acid solution was added
  5. filtrationThe resulting crystals were collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-16dccbe6dce14a94980063ae30240c3f
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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