Tert-butyl 3-(2-aminoacetamido)azetidine-1-carboxylate → Tert-butyl 3-(2-((2,6-bis(trifluoromethyl)quinazolin-4-yl)amino)acetamido)azetidine-1-carboxylate

HRID 1896908Notes

Reaction equation

HRID 1896908 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[N:5]=[C:4]([C:16]([F:19])([F:18])[F:17])[N:3]=1.[NH2:20][CH2:21][C:22]([NH:24][CH:25]1[CH2:28][N:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:26]1)=[O:23]>C1COCC1>[F:17][C:16]([F:19])([F:18])[C:4]1[N:3]=[C:2]([NH:20][CH2:21][C:22]([NH:24][CH:25]2[CH2:28][N:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:26]2)=[O:23])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[N:5]=1

Participants

4

Reactant 2

HCID 18699815Tert-butyl 3-(2-aminoacetamido)azetidine-1-carboxylateHCID 341762704-Chloro-2,6-bis(trifluoromethyl)quinazoline

Product 1

HCID 71552538Tert-butyl 3-(2-((2,6-bis(trifluoromethyl)quinazolin-4-yl)amino)acetamido)azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-chloro-2,6-bis(trifluoromethyl)quinazoline (120 mg, 0.399 mmol, prepared in the previous step), tert-butyl 3-(2-aminoacetamido)azetidine-1-carboxylate (133 mg, 0.58 mmol, prepared in Example 1, Step E) and TEA (0.12 mL, 0.863 mmol) was dissolved in dry THF (10 mL) and heated to reflux under argon for 18 hours. The reaction mixture as concentrated in vacuo and the residue purified by flash chromatography (silica gel, 50% EtOAc/Heptane).

Workup

  1. temperatureheated
  2. temperatureto reflux under argon for 18 hours
  3. concentrationThe reaction mixture as concentrated in vacuo
  4. customthe residue purified by flash chromatography (silica gel, 50% EtOAc/Heptane)

Sources & evidence

ORD record
ord-11478d0c622d475197d4b1fcc2760fd2
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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