Ethyl chloroformate → HCID 86649611, compound

HRID 2282258Notes

Reaction equation

HRID 2282258 reaction equation
[CH2:1]([O:3][C:4]1[N:5]=[C:6]([C:20]2[CH:25]=[CH:24][N:23]=[C:22]([NH2:26])[CH:21]=2)[S:7][C:8]=1[C:9]1[N:13]=[CH:12][N:11]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[N:10]=1)[CH3:2].Cl[C:28]([O:30][CH2:31][CH3:32])=[O:29]>N1C=CC=CC=1.O>[CH2:1]([O:3][C:4]1[N:5]=[C:6]([C:20]2[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C:28](=[O:29])[O:30][CH2:31][CH3:32])[CH:21]=2)[S:7][C:8]=1[C:9]1[N:13]=[CH:12][N:11]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[N:10]=1)[CH3:2]

Participants

5

Reactant 2

HCID 10928Ethyl chloroformateHCID 66855196HCID 66855196, compound

Product 1

HCID 86649611HCID 86649611, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a solution of 4-{4-ethoxy-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-1,3-thiazol-2-yl}pyridin-2-amine (100 mg, 0.268 mmol) obtained by similar manner with Example 47-B(ii) in pyridine (2.7 mL), was added ethyl chloroformate (100 μL, 1.08 mmol) at 0° C., and the mixture was stirred for 3 h. The reaction mixture was diluted with water (20 mL), and the mixture was stirred for 1 h. The resulting precipitate was collected by filtration and was washed with water and diethyl ether to give the title compound (99.1 mg, 83%) as a yellow solid.

Workup

  1. stirringthe mixture was stirred for 1 h
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwas washed with water and diethyl ether

Sources & evidence

ORD record
ord-509e751d5fb745268ae2b536bb071f6f
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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