Triethylamine → Tert-butyl 3-(2-(methyl(6-(trifluoromethyl)quinazolin-4-yl)amino)acetamido)azetidine-1-carboxylate

HRID 2175575Notes

Reaction equation

HRID 2175575 reaction equation
[CH3:1][NH:2][CH2:3][C:4]([NH:6][CH:7]1[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8]1)=[O:5].Cl[C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([C:29]([F:32])([F:31])[F:30])[CH:27]=2)[N:22]=[CH:21][N:20]=1.C(N(CC)CC)C>CC(O)C>[CH3:1][N:2]([C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([C:29]([F:31])([F:32])[F:30])[CH:27]=2)[N:22]=[CH:21][N:20]=1)[CH2:3][C:4]([NH:6][CH:7]1[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8]1)=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18699830Tert-butyl 3-(2-(methylamino)acetamido)azetidine-1-carboxylateHCID 210750954-Chloro-6-(trifluoromethyl)quinazoline

Product 1

HCID 68004072Tert-butyl 3-(2-(methyl(6-(trifluoromethyl)quinazolin-4-yl)amino)acetamido)azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of tert-butyl 3-(2-(methylamino)acetamido)azetidine-1-carboxylate (348 mg, 1.43 mmol) as prepared in the previous step and commercially available 4-chloro-6-(trifluoromethyl)quinazoline (327 mg, 1.41 mmol) were stirred in anhydrous iPrOH and triethylamine at 90° C. under argon for 1 hour. The reaction mixture was concentrated in vacuo and the residue purified by flash chromatography (silica gel, 0%-5% MeOH/EtOAc) to give a yellow solid after drying under high vac.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue purified by flash chromatography (silica gel, 0%-5% MeOH/EtOAc)
  3. customto give a yellow solid
  4. customafter drying under high vac

Sources & evidence

ORD record
ord-3f8f3085568e4aac95e23ffa882a5694
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

Loading…