Azetidine → HCID 59420713, compound

HRID 499091Notes

Reaction equation

HRID 499091 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:13]=[C:12]([CH2:14][CH2:15]Br)[N:11]=[C:10]([S:17][C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:28])[CH2:26][CH3:27])=[CH:20][CH:19]=3)[N:9]=2)[CH:3]=1.[NH:29]1[CH2:32][CH2:31][CH2:30]1>CN(C)C=O.C(OCC)(=O)C>[CH3:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:13]=[C:12]([CH2:14][CH2:15][N:29]3[CH2:32][CH2:31][CH2:30]3)[N:11]=[C:10]([S:17][C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:28])[CH2:26][CH3:27])=[CH:20][CH:19]=3)[N:9]=2)[CH:3]=1

Participants

5

Reactant 2

HCID 10422AzetidineHCID 59420850HCID 59420850, compound

Product 1

HCID 59420713HCID 59420713, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-(4-(4-(5-methyl-1H-pyrazol-3-ylamino)-6-(2-bromoethyl)pyrimidin-2-ylthio)phenyl)propionamide (100 mg, 0.21 mmol) and azetidine (36 mg, 0.63 mmol) in dimethylformamide (2 ml) was stirred at room temperature under a nitrogen atmosphere for 24 hours. The reaction mixture was diluted with ethyl acetate (40 ml). The organic layer was washed with a saturated solution of sodium bicarbonate (10 ml) and brine (10 ml), then dried over magnesium sulfate. The residue was purified by Gilson HPLC to afford the title compound as a bis-trifluoro acetic acid salt (0.5 mg, 1%). 1H NMR (CD3OD): 1.30-1.37 (3H, m), 2.15-2.20 (3H, s), 2.40-2.50 (4H, m), 2.80-2.90 (2H, t), 3.50-3.55 (2H, t), 4.00-4.15 (4H, s), 6.50-6.55 (1H, s), 7.55-7.65 (2H, m), 7.75-7.80 (2H, m). ES+ 438

Workup

  1. washThe organic layer was washed with a saturated solution of sodium bicarbonate (10 ml) and brine (10 ml)
  2. dry with materialdried over magnesium sulfate
  3. customThe residue was purified by Gilson HPLC

Sources & evidence

ORD record
ord-e6cf8f9e96854fc484acb4cba3dccbaf
Source dataset
uspto-grants-2010_08
Patent number
US07767672B2

Reaction notes

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