Tert-butyl 3-aminoazetidine-1-carboxylate → HCID 58777638, compound

HRID 1371775Notes

Reaction equation

HRID 1371775 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[C:12]([F:18])[C:11]=2[F:19])=[O:9])=[CH:6][N:5]=[C:4](Cl)[N:3]=1.[C:21]([O:25][C:26]([N:28]1[CH2:31][CH:30]([NH2:32])[CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22]>C(Cl)Cl.C(O)C>[C:21]([O:25][C:26]([N:28]1[CH2:31][CH:30]([NH:32][C:4]2[N:3]=[C:2]([NH2:1])[C:7]([C:8](=[O:9])[C:10]3[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[C:12]([F:18])[C:11]=3[F:19])=[CH:6][N:5]=2)[CH2:29]1)=[O:27])([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 2

HCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylateHCID 21070550HCID 21070550, compound

Product 1

HCID 58777638HCID 58777638, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred suspension of chloropyrimidine (700 mg, 2.34 mmol, Example 289) in methylene chloride (30 mL), amine (525 mg, 5.64 mmol, Example 318) in ethanol (30 mL) was added and the mixture heated at 80° C. for 4.5 hours. The solvent was removed and the residue was dissolved in ethyl acetate and the mixture was washed successively with 0.5N hydrochloric acid and water. The organic layer was dried with sodium sulfate and concentrated to give a white solid. 1.0 g, 98%. MS (ES) MH+=436.

Workup

  1. additionwas added
  2. customThe solvent was removed
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washthe mixture was washed successively with 0.5N hydrochloric acid and water
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. concentrationconcentrated
  7. customto give a white solid

Sources & evidence

ORD record
ord-dd962719fdbd4bd0bc96e9960a153395
Source dataset
uspto-grants-2007_01
Patent number
US07157455B2

Reaction notes

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