Ethyl chloroformate → HCID 73052232, compound

HRID 1497794Notes

Reaction equation

HRID 1497794 reaction equation
[NH2:1][C:2]1[N:34]=[C:5]2[C:6]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=3)=[C:7]([CH3:23])[C:8]([C:10]3[N:14]([C:15]4[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=4)[N:13]=[CH:12][CH:11]=3)=[CH:9][N:4]2[N:3]=1.Cl[C:36]([O:38][CH2:39][CH3:40])=[O:37]>N1C=CC=CC=1>[CH2:39]([O:38][C:36](=[O:37])[NH:1][C:2]1[N:34]=[C:5]2[C:6]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:32])([F:33])[F:31])[CH:25]=3)=[C:7]([CH3:23])[C:8]([C:10]3[N:14]([C:15]4[CH:16]=[CH:17][C:18]([C:19]#[N:20])=[CH:21][CH:22]=4)[N:13]=[CH:12][CH:11]=3)=[CH:9][N:4]2[N:3]=1)[CH3:40]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 730509764-{5-[2-Amino-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-pyrazol-1-yl}-benzonitrile

Product 1

HCID 73052232HCID 73052232, compoundYield 20.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4-{5-[2-amino-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-pyrazol-1-yl}-benzonitrile (Ex. 1, 100 mg, 0.218 mmol) and ethyl chloroformate (104 μL, 1.089 mmol) in pyridine (2.5 mL) was heated at 120° C. for 20 mins using microwave irradiation. The reaction mixture was azeotroped with toluene in vacuo. The resultant residue was subjected to preparative C18 HPLC, eluting with a gradient of 40-80% MeCN in water (+0.1% formic acid) to give the title compound as a white solid (24 mg).

Workup

  1. custommicrowave irradiation
  2. customThe reaction mixture was azeotroped with toluene in vacuo
  3. washeluting with a gradient of 40-80% MeCN in water (+0.1% formic acid)

Sources & evidence

ORD record
ord-8aec4e92e75b4561b679f5b3b528f975
Source dataset
uspto-grants-2015_12
Patent number
US09199984B2

Reaction notes

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