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

HRID 2175488Notes

Reaction equation

HRID 2175488 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][CH:6]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]1)=[O:4].Cl[C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:28]([F:31])([F:30])[F:29])[CH:26]=2)[N:21]=[CH:20][N:19]=1.C(N(CC)CC)C>CC(O)C>[F:31][C:28]([F:29])([F:30])[C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][N:19]=[C:18]2[NH:1][CH2:2][C:3]([NH:5][CH:6]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18699815Tert-butyl 3-(2-aminoacetamido)azetidine-1-carboxylateHCID 210750954-Chloro-6-(trifluoromethyl)quinazoline

Product 1

HCID 58562886Tert-butyl 3-(2-(6-(trifluoromethyl)quinazolin-4-ylamino)acetamido)azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of tert-butyl 3-(2-aminoacetamido)azetidine-1-carboxylate (1.073 g, 4.682 mmol) as prepared in the previous step and commercially available 4-chloro-6-(trifluoromethyl)quinazoline (990 mg, 4.256 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 vacuum.

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 vacuum

Sources & evidence

ORD record
ord-90f2ba1d486a45808adccf334caa1c52
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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