Cyclopropanemethanamine → 1-(Cyclopropylmethyl)-3-(3-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-ylsulfonyl)phenyl)urea

HRID 1807812Notes

Reaction equation

HRID 1807812 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([OH:33])([C:29]([F:32])([F:31])[F:30])[C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=3)[CH2:13][CH2:12]2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[C:34](Cl)(=O)[O:35]C1C=CC([N+]([O-])=O)=CC=1.[CH:47]1([CH2:50][NH2:51])[CH2:49][CH2:48]1>ClCCl.CN(C)C=O>[CH:47]1([CH2:50][NH:51][C:34]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([S:8]([N:11]3[CH2:12][CH2:13][N:14]([CH2:17][C:18]4[CH:19]=[CH:20][C:21]([C:24]([OH:33])([C:25]([F:26])([F:27])[F:28])[C:29]([F:32])([F:31])[F:30])=[CH:22][CH:23]=4)[CH2:15][CH2:16]3)(=[O:9])=[O:10])[CH:3]=2)=[O:35])[CH2:49][CH2:48]1

Participants

5

Reactant 3

HCID 75646CyclopropanemethanamineHCID 821294-Nitrophenyl chloroformateHCID 866385882-(4-((4-(3-Aminophenylsulfonyl)piperazin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 591759041-(Cyclopropylmethyl)-3-(3-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-ylsulfonyl)phenyl)ureaYield 29.1%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

2-(4-((4-(3-Aminophenylsulfonyl)piperazin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.302 mmol, 150 mg) and 4-nitrophenyl carbonochloridate (0.302 mmol, 60.8 mg) were combined in a mixture of dichloromethane/dimethylformamide and stirred at room temperature for 1 hour. Cyclopropylmethanamine (0.603 mmol, 42.9 mg) was added and the reaction mixture was left to stir at room temperature for 15 minutes. The reaction mixture was purified by SCX chromatography and concentrated under vacuum. The residue was purified by silica column chromatography, eluting with 0%-4% methanol/dichloromethane gradient, to afford the title compound (52.3 mg).

Workup

  1. waitthe reaction mixture was left
  2. stirringto stir at room temperature for 15 minutes
  3. customThe reaction mixture was purified by SCX chromatography
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by silica column chromatography
  6. washeluting with 0%-4% methanol/dichloromethane gradient

Sources & evidence

ORD record
ord-6a1ea11b08684ee8927e94d96fa3b685
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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