N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine → HCID 178474439, compound

HRID 1246492Notes

Reaction equation

HRID 1246492 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:19]([OH:21])=[O:20])=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2].C[Si](C([Si](C)(C)C)C(N)=O)(C)C.[C:34]([O:38][C:39]([NH:41][C:42](N1C=CC=N1)=[N:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[O:40])([CH3:37])([CH3:36])[CH3:35]>C1COCC1>[C:1]([NH:4][C:5]1[S:6][C:7]([C:19]([OH:21])=[O:20])=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18]/[C:42](/[NH:41][C:39]([O:38][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:40])=[N:43]/[C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 4428040N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidineHCID 11708267BistrimethylsilylacetamidHCID 219152482-(Acetylamino)-4-[2-(4-aminophenyl)ethyl]-1,3-thiazole-5-carboxylic acid

Product 1

HCID 178474439HCID 178474439, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(Acetylamino)-4-[2-(4-aminophenyl)ethyl]-1,3-thiazole-5-carboxylic acid (106 mg) was suspended in THF (2 ml) under N2 atmosphere. Bis(trimethylsilyl)acetamide (0.253 ml) was added to the suspension at r.t., and the mixture was stirred at r.t. for 15 minutes. Then, N,N′-bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine (119 mg) was added to the solution at r.t. The reaction mixture was stirred at r.t. for 20 hours, and concentrated in vacuo. The residue was dissolved in CHCl3. The organic solution was washed with 1N-HCl, water and brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residual solid was washed with ethyl ether to give 2-(acetylamino)-4-{2-[4-({(Z)-[(tert-butoxycarbonyl)amino](tert-butoxycarbonyl)iminomethyl}amino)phenyl]ethyl}-1,3-thiazole-5-carboxylic acid (115.8 mg) as a pale brown solid.

Workup

  1. stirringThe reaction mixture was stirred at r.t. for 20 hours
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in CHCl3
  4. washThe organic solution was washed with 1N-HCl, water and brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo
  7. washThe residual solid was washed with ethyl ether

Sources & evidence

ORD record
ord-2a854a60231e4bfaa55c2d16d8de4724
Source dataset
uspto-grants-2006_10
Patent number
US07125901B2

Reaction notes

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