Ammonia → HCID 57919990, compound

HRID 1882449Notes

Reaction equation

HRID 1882449 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][N:10]([C:13]2[S:14][C:15]([C:19](O)=[O:20])=[C:16]([CH3:18])[N:17]=2)[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N:24]1CCOCC1.ClC(OCC(C)C)=O.N>O1CCCC1>[CH2:1]([N:8]1[CH2:12][CH2:11][N:10]([C:13]2[S:14][C:15]([C:19]([NH2:24])=[O:20])=[C:16]([CH3:18])[N:17]=2)[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 57919990HCID 57919990, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid (1.50 g, 4.72 mmol) and 4-methylmorpholine (0.60 mL, 5.45 mmol) in tetrahydrofuran (100 mL) was added isobutyl chloroformate (0.62 mL, 4.73 mmol) at 0° C. The resulting mixture was stirred at ambient temperature for 1 hour and followed by the addition of ammonia (7.0 N solution in methanol, 10 mL, 70 mmol). The reaction mixture was kept stirring at ambient temperature for 19 hours. The solvent was removed in vacuo and the residue was triturated with 10% sodium hydroxide solution. The solid was collected by filtration and washed with water to afford the title compound in 30% yield (0.47 g): mp 217-218° C. (water); 1H NMR (300 MHz, DMSO-d6) δ 7.42-7.27 (m, 7H), 4.40 (s, 2H), 3.93-3.88 (m, 2H), 3.48-3.42 (m, 2H), 2.42 (s, 3H); MS (ES+) m/z 317.2 (M+1).

Workup

  1. stirringThe reaction mixture was kept stirring at ambient temperature for 19 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue was triturated with 10% sodium hydroxide solution
  4. filtrationThe solid was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-f006c1efad204bbf96da468497c8ff53
Source dataset
uspto-grants-2012_11
Patent number
US08318949B2

Reaction notes

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