Water → HCID 87393674, compound

HRID 658041Notes

Reaction equation

HRID 658041 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[C:7]([O:11][C:12]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:21][C:22](=[O:40])[C:23]1[CH:28]=[CH:27][C:26]([CH2:29][NH:30][CH2:31]CCN2CCOCC2)=[CH:25][CH:24]=1)=[O:13])([CH3:10])([CH3:9])[CH3:8].[OH2:41].[CH2:42]1[CH2:46][O:45][CH2:44][CH2:43]1>>[C:7]([O:11][C:12]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:21][C:22](=[O:40])[C:23]1[CH:24]=[CH:25][C:26]([CH:29]([NH:30][C:31]([NH:1][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)=[O:41])[CH2:17][CH2:16][CH2:15][N:14]2[CH2:42][CH2:46][O:45][CH2:44][CH2:43]2)=[CH:27][CH:28]=1)=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 4

HCID 962WaterHCID 21552-AminothiazoleHCID 8028TetrahydrofuranHCID 58001277HCID 58001277, compound

Product 1

HCID 87393674HCID 87393674, compoundYield 65%

Procedure

Under ice cooling, 2-aminothiazole (65 mg, 0.64 mmol) was added to a solution of N,N′-carbonyldiimidazole (110 mg, 0.68 mmol) in THF (3.0 mL), and then the reaction mixture was stirred for 6 hours. N-(2-t-butoxycarbonylaminophenyl)-4-[3-(morpholin-4-yl) propylaminomethyl]benzamide (Reference Compound No. 4-11, 110 mg, 0.23 mmol) was added thereto, and then the reaction mixture was stirred at 60° C. for 16 hours. Water (100 mL) was added thereto, the whole was extracted with ethyl acetate (100 mL), and then the organic layer was washed with brine (100 mL). The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-methanol) to give 90 mg of the title reference compound as a colorless amorphous product. (Yield 65%)

Workup

  1. stirringthe reaction mixture was stirred at 60° C. for 16 hours
  2. extractionthe whole was extracted with ethyl acetate (100 mL)
  3. washthe organic layer was washed with brine (100 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform-methanol)
  7. customto give 90 mg of the title reference compound as a colorless amorphous product

Sources & evidence

ORD record
ord-7998306f4a37444fa44e0e3e8ac5396f
Source dataset
uspto-grants-2011_12
Patent number
US08076332B2

Reaction notes

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