Diisopropylethylamine → tert-butyl [1-(([1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino]carbonyl)-3-azetidinyl]carbamate

HRID 1247819Notes

Reaction equation

HRID 1247819 reaction equation
[CH3:1][N:2]1[C:6]([NH:7][C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:5]([NH:27][C:28](=O)[O:29]C2C=CC=CC=2)[CH:4]=[N:3]1.C(O)(=O)C.[NH:41]1[CH2:44][CH:43]([NH:45][C:46](=[O:52])[O:47][C:48]([CH3:51])([CH3:50])[CH3:49])[CH2:42]1.C(N(C(C)C)C(C)C)C>C(Cl)Cl>[CH3:1][N:2]1[C:6]([NH:7][C:8]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[C:5]([NH:27][C:28]([N:41]2[CH2:44][CH:43]([NH:45][C:46](=[O:52])[O:47][C:48]([CH3:49])([CH3:51])[CH3:50])[CH2:42]2)=[O:29])[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 21904480Tert-butyl azetidin-3-ylcarbamate acetateHCID 21904567Phenyl [1-methyl-5-(tritylamino)pyrazol-4-yl]carbamate

Product 1

HCID 86593409tert-butyl [1-(([1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino]carbonyl)-3-azetidinyl]carbamateYield 88.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of phenyl [1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]carbamate (711 mg) and tert-butyl 3-azetidinylcarbamate acetic acid salt (418 mg) in methylene chloride (8 ml) was added N-ethyldiisopropylamine (0.62 ml), and the mixture was stirred under reflux for 16 hours. To the reaction mixture was added methylene chloride, and the solution was washed successively with 10% aqueous citric acid solution, 10% aqueous sodium hydroxide solution and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was triturated with a mixed solvent of ethyl acetate and hexane to give tert-butyl [1-({[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}carbonyl)-3-azetidinyl]carbamate (735 mg) as a solid;

Workup

  1. temperatureunder reflux for 16 hours
  2. washthe solution was washed successively with 10% aqueous citric acid solution, 10% aqueous sodium hydroxide solution and brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-5a7f5315dcbf48108d3bf394f4c5060e
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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