Water → Tert-butyl 2-{[4-({[2-(acetylamino)-1,3-thiazol-4-yl]carbonyl}amino)benzyl]carbamoyl}hydrazinecarboxylate

HRID 1892530Notes

Reaction equation

HRID 1892530 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([C:10]([OH:12])=O)[N:9]=1)(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:25][C:26]1[CH:44]=[CH:43][C:29]([CH2:30][NH:31][C:32]([NH:34][NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[O:33])=[CH:28][CH:27]=1.O>O1CCCC1.CN(C)C=O.C(OCC)(=O)C>[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([C:10]([NH:25][C:26]2[CH:27]=[CH:28][C:29]([CH2:30][NH:31][C:32]([NH:34][NH:35][C:36]([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])=[O:37])=[O:33])=[CH:43][CH:44]=2)=[O:12])[N:9]=1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 962WaterHCID 682631,1'-Carbonyldiimidazole2×HCID 8401132-Acetamido-1,3-thiazole-4-carboxylic acid2×HCID 66862751Tert-butyl 2-[(4-aminobenzyl)carbamoyl]hydrazinecarboxylate

Product 1

HCID 86650035Tert-butyl 2-{[4-({[2-(acetylamino)-1,3-thiazol-4-yl]carbonyl}amino)benzyl]carbamoyl}hydrazinecarboxylateYield 90.9%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 2-(acetylamino)-1,3-thiazole-4-carboxylic acid (558.6 mg, 3.000 mmol) in anhydrous tetrahydrofuran (10 ml) were added 1,1′-carbonyldiimidazole (535.2 mg, 3.301 mmol) and anhydrous tetrahydrofuran (10 ml), and the mixture was stirred at 50° C. for 2 hr. tert-Butyl 2-[(4-aminobenzyl)carbamoyl]hydrazinecarboxylate (841.0 mg, 3.000 mmol) was added, and the mixture was stirred for 24 hr. To a solution of 2-(acetylamino)-1,3-thiazole-4-carboxylic acid (280.2 mg, 1.505 mmol) in anhydrous N,N-dimethylformamide (5 ml) was added 1,1′-carbonyldiimidazole (243.2 mg, 1.500 mmol), and the mixture was stirred at 50° C. for 30 min. This solution was added to the mixture obtained above, and the mixture was stirred at 50° C. for 3 hr, and at room temperature for 65 hr. Water and ethyl acetate were added to the reaction mixture and the mixture was stirred. The precipitated solid was filtered, washed with ethyl acetate, and dried under reduced pressure to give tert-butyl 2-{[4-({[2-(acetylamino)-1,3-thiazol-4-yl]carbonyl}amino)benzyl]carbamoyl}hydrazinecarboxylate (1.223 g, 2.728 mmol, yield 90.9%) as a white solid.

Workup

  1. stirringthe mixture was stirred for 24 hr
  2. stirringthe mixture was stirred at 50° C. for 30 min
  3. additionThis solution was added to the mixture
  4. customobtained above, and the mixture
  5. stirringwas stirred at 50° C. for 3 hr
  6. waitat room temperature for 65 hr
  7. stirringthe mixture was stirred
  8. filtrationThe precipitated solid was filtered
  9. washwashed with ethyl acetate
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-9f44db9c26654cebb26c2ea592e61eab
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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