HCID 22101094, compound → HCID 178469935, compound

HRID 1457927Notes

Reaction equation

HRID 1457927 reaction equation
[C:1]1([NH:7][C:8]([NH:10][C:11]2[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][N:13](C(OC(C)(C)C)=O)[N:12]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>FC(F)(F)C(O)=O.ClCCl>[C:1]1([NH:7][C:8]([NH:10][C:11]2[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][NH:13][N:12]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 22101094HCID 22101094, compound2×

Product 1

HCID 178469935HCID 178469935, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 3-amino-4-ethoxycarbonylpyrazole (1.0 g) in THF (10 ml), was added di-tert-butyl dicarbonate (2.2 g), and the mixture was stirred overnight at room temperature. The reaction mixture was evaporated under reduced pressure followed by silica-gel column chromatography (toluene/ethyl acetate=15/1) to give 3-amino-1(tert-butoxycarbonyl)-4-ethoxycarbonylpyrazole (0.59 g). This intermediate was derived to N-phenyl-N'-(1-tert-butoxycarbonyl-4-ethoxycarbonylpyrazol-3-yl)urea by the similar method to Reference Example 1 (yield 75%). N-phenyl-N'-(1-tertbutoxycarbonyl-4-ethoxycarbonylpyrazol-3-yl)urea (0.5 g) was dissolved in a solution of 10% trifluoroacetic acid in dichloromethane (7 ml), and the resulted solution was stirred overnight at room temperature. The reaction mixture was evaporated under reduced pressure followed by addition of ether to give the title compound (0.304 g, yield 83%).

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. additionfollowed by addition of ether

Sources & evidence

ORD record
ord-5e15fa51cf304fdab89a9dad5ff93bde
Source dataset
uspto-grants-1998_12
Patent number
US05849779

Reaction notes

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