Water → tert-butyl [(3E)-4-cyano-3-({[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}carbonyl)-3-buten-1-yl]carbamate

HRID 459623Notes

Reaction equation

HRID 459623 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[CH3:14][N:15]1[C:19]([NH:20][C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([NH:40][C:41](=[O:54])[C:42](=O)[CH2:43][CH2:44][NH:45][C:46](=[O:52])[O:47][C:48]([CH3:51])([CH3:50])[CH3:49])[CH:17]=[N:16]1.O>O1CCCC1>[C:1](/[CH:3]=[C:42](/[C:41]([NH:40][C:18]1[CH:17]=[N:16][N:15]([CH3:14])[C:19]=1[NH:20][C:21]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:54])\[CH2:43][CH2:44][NH:45][C:46](=[O:52])[O:47][C:48]([CH3:49])([CH3:51])[CH3:50])#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 86597878tert-butyl (4-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3,4-dioxobutyl)carbamate

Product 1

HCID 86597879tert-butyl [(3E)-4-cyano-3-({[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}carbonyl)-3-buten-1-yl]carbamateYield 67.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of diethyl (cyanomethyl)phosphonate (704 mg) in tetrahydrofuran (20 ml) was added sodium hydride (159 mg, 60% oil suspension) under ice-cooling. The mixture was stirred for 45 minutes with warming to room temperature. tert-Butyl (4-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3,4-dioxobutyl)carbamate (2 g) was added to the mixture, and the whole mixture was stirred at room temperature for 2 hours. Water was added to the mixture, and the whole mixture was extracted with ethyl acetate. The extract was washed with water and brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a residual oil, which was triturated with a small amount of ethyl acetate and diluted with diisopropyl ether. The resulting precipitate was collected by filtration to give tert-butyl [(3E)-4-cyano-3-({[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}carbonyl)-3-buten-1-yl]carbamate (1.41 g).

Workup

  1. temperaturecooling
  2. stirringthe whole mixture was stirred at room temperature for 2 hours
  3. extractionthe whole mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customto give a residual oil, which
  8. customwas triturated with a small amount of ethyl acetate
  9. additiondiluted with diisopropyl ether
  10. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-a2a04bead5ee4113b5640c4f61f770a9
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

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