2-Aminothiazole → HCID 178500665, compound

HRID 1713752Notes

Reaction equation

HRID 1713752 reaction equation
[C:1](C1NC=CN=1)(C1NC=CN=1)=S.[NH2:13][C:14]1[S:15][CH:16]=[CH:17][N:18]=1.[NH:19]([C:21](=[O:42])[C:22]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([C@H:31]2[CH2:36][CH2:35][C@H:34]([CH2:37][C:38]([O:40][CH3:41])=[O:39])[CH2:33][CH2:32]2)=[CH:27][CH:26]=1)=[O:23])[NH2:20].CCN=C=NCCCN(C)C>CC(N(C)C)=O.O>[S:15]1[CH:16]=[CH:17][N:18]=[C:14]1[NH:13][C:1]1[O:42][C:21]([C:22]([NH:24][C:25]2[CH:26]=[CH:27][C:28]([C@H:31]3[CH2:32][CH2:33][C@H:34]([CH2:37][C:38]([O:40][CH3:41])=[O:39])[CH2:35][CH2:36]3)=[CH:29][CH:30]=2)=[O:23])=[N:19][N:20]=1

Participants

7

Reactant 4

HCID 21552-AminothiazoleHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 11412697Thiocarbonyl diimidazoleHCID 178500682HCID 178500682, compound2×

Product 1

HCID 178500665HCID 178500665, compoundYield 36.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

Thiocarbonyl diimidazole (179 mg, 1.00 mmol) was added in one portion to a solution of 2-aminothiazole (100 mg, 1.00 mmol) in DMA (5 mL) and the solution was stirred at room temperature for 6 h. Methyl [trans-4-(4-{[hydrazino(oxo)acetyl]amino}phenyl)cyclohexyl]-acetate (Intermediate 43, 267 mg, 0.80 mmol) was added in one portion and the reaction mixture was stirred at room temperature for 20 h and then heated at 80° C. for 10 minutes in the microwave. The solution was cooled to room temperature and EDCI (192 mg, 1.00 mmol) was added in one portion and the reaction mixture was heated to 90° C. for 15 minutes in the microwave. The reaction mixture was cooled to room temperature and poured into water (200 mL). The mixture was filtered and the resulting solid was recrystallised (CH3CN) to give the title compound (130 mg, 29%) as a solid; 1H NMR δ 1.09-1.18 (2H, m), 1.42-1.47 (2H, m), 1.79 (5H, m), 2.24-2.26 (2H, d), 2.45 (1H, t), 3.61 (3H, s), 6.99 (1H, d), 7.22 (2H, d), 7.38 (1H, d), 7.67-7.70 (2H, m), 10.78 (1H, s);

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 20 h
  2. temperatureheated at 80° C. for 10 minutes in the microwave
  3. temperatureThe solution was cooled to room temperature
  4. temperaturethe reaction mixture was heated to 90° C. for 15 minutes in the microwave
  5. temperatureThe reaction mixture was cooled to room temperature
  6. filtrationThe mixture was filtered
  7. customthe resulting solid was recrystallised (CH3CN)

Sources & evidence

ORD record
ord-42b4f57e748745ec88bdc689054f5203
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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