4-Nitrophenyl chloroformate → 1-(4-(4-(4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carbonyl)phenyl)-3-(2-hydroxy-2-methylpropyl)urea

HRID 1807714Notes

Reaction equation

HRID 1807714 reaction equation
[C:1](Cl)(=O)[O:2]C1C=CC([N+]([O-])=O)=CC=1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([N:23]2[CH2:28][CH2:27][N:26]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([C:36]([OH:45])([C:41]([F:44])([F:43])[F:42])[C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=3)[CH2:25][CH2:24]2)=[O:22])=[CH:17][CH:16]=1.[NH2:46][CH2:47][C:48]([CH3:51])([OH:50])[CH3:49]>ClCCl>[F:42][C:41]([F:44])([F:43])[C:36]([C:33]1[CH:32]=[CH:31][C:30]([CH2:29][N:26]2[CH2:27][CH2:28][N:23]([C:21]([C:18]3[CH:17]=[CH:16][C:15]([NH:14][C:1]([NH:46][CH2:47][C:48]([OH:50])([CH3:51])[CH3:49])=[O:2])=[CH:20][CH:19]=3)=[O:22])[CH2:24][CH2:25]2)=[CH:35][CH:34]=1)([OH:45])[C:37]([F:38])([F:39])[F:40]

Participants

5

Reactant 3

HCID 821294-Nitrophenyl chloroformateHCID 951022-Propanol, 1-amino-2-methyl-HCID 86638547(4-Aminophenyl)(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-yl)methanone

Product 1

HCID 591759091-(4-(4-(4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carbonyl)phenyl)-3-(2-hydroxy-2-methylpropyl)ureaYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Nitrophenyl carbonochloridate (0.217 mmol, 43.7 mg) was added to a stirred solution of (4-aminophenyl)(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)-piperazin-1-yl)methanone (0.217 mmol, 100 mg) in dichloromethane (1 mL). After 1 hour, 1-amino-2-methylpropan-2-ol (0.650 mmol, 58.0 mg) was added and stirring continued for 1 hour. The reaction mixture was purified by silica column chromatography (eluant dichloromethane/methanol 0% to 10%) to yield the title compound (30 mg).

Workup

  1. waitcontinued for 1 hour
  2. customThe reaction mixture was purified by silica column chromatography (eluant dichloromethane/methanol 0% to 10%)

Sources & evidence

ORD record
ord-a04dcdcba8114cc6a94bd72b18fb446d
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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