Ethyl Acetate → tert-butyl (2-{N-({[1-methyl-5-(tritylamino)pyrazol-4-yl]amino}carbonyl)-N-[2-(tritylamino)ethyl]amino}ethyl)carbamate

HRID 459609Notes

Reaction equation

HRID 459609 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:37]([NH:56][CH2:57][CH2:58][NH:59][CH2:60][CH2:61][NH:62][C:63](=[O:69])[O:64][C:65]([CH3:68])([CH3:67])[CH3:66])([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C(N(C(C)C)C(C)C)C.C(OCC)(=O)C>C(Cl)(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:59]([CH2:60][CH2:61][NH:62][C:63](=[O:69])[O:64][C:65]([CH3:66])([CH3:68])[CH3:67])[CH2:58][CH2:57][NH:56][C:37]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:29])[CH:4]=[N:3]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 18442413Tert-butyl 2-{[2-(tritylamino)ethyl]amino}ethylcarbamateHCID 21904567Phenyl [1-methyl-5-(tritylamino)pyrazol-4-yl]carbamate

Product 1

HCID 86597868tert-butyl (2-{N-({[1-methyl-5-(tritylamino)pyrazol-4-yl]amino}carbonyl)-N-[2-(tritylamino)ethyl]amino}ethyl)carbamateYield 92.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of phenyl [1-methyl-5-(tritylamino)pyrazol-4-yl]carbamate (712 mg) and tert-butyl 2-{[2-(tritylamino)ethyl]amino}ethylcarbamate (668 mg) in dehydrated chloroform (4 ml) was added N-ethyldiisopropylamine (0.257 ml), and the mixture was stirred under reflux for 16 hours. To the reaction mixture was added ethyl acetate, and the solution was washed successively with water, 5% aqueous citric acid solution, 1M aqueous sodium hydroxide solution and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with 5% methanol/methylene chloride to give tert-butyl (2-{N-({[1-methyl-5-(tritylamino)pyrazol-4-yl]amino}carbonyl)-N-[2-(tritylamino)ethyl]amino}ethyl)carbamate (1.15 g) as a solid.

Workup

  1. temperatureunder reflux for 16 hours
  2. washthe solution was washed successively with water, 5% aqueous citric acid solution, 1M aqueous sodium hydroxide solution and brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with 5% methanol/methylene chloride

Sources & evidence

ORD record
ord-db8d5ac858ce446b8fe4a16a94e89c29
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

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