Isopropylamine → HCID 59175889, compound

HRID 1807706Notes

Reaction equation

HRID 1807706 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])[CH:18]=3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[C:33](Cl)(=O)[O:34]C1C=CC([N+]([O-])=O)=CC=1.[CH:46]([NH2:49])([CH3:48])[CH3:47]>C(#N)C>[F:29][C:28]([F:31])([F:30])[C:23]([C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[CH2:16][N:13]1[CH2:14][CH2:15][N:10]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:33]([NH:49][CH:46]([CH3:48])[CH3:47])=[O:34])=[CH:3][CH:4]=2)=[O:9])[CH2:11][CH2:12]1)([OH:32])[C:24]([F:25])([F:26])[F:27]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 821294-Nitrophenyl chloroformateHCID 59175857HCID 59175857, compound

Product 1

HCID 59175889HCID 59175889, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(4-Aminophenyl)(4-(3-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)-piperazin-1-yl)methanone (131 mg, 0.28 mmol) was dissolved in acetonitrile (5 mL) and treated with 4-nitrophenyl carbonochloridate (57.8 mg, 0.29 mmol). This was stirred at room temperature for 1 hour before isopropylamine (0.121 mL, 1.42 mmol) was added. The reaction was stirred for a further 2 hours at room temperature, filtered and concentrated under vacuum. The mixture was purified by HPLC and then treated with strong cation exchange column chromatography to afford the title compound (17.0 mg).

Workup

  1. additionwas added
  2. filtrationfiltered
  3. concentrationconcentrated under vacuum
  4. customThe mixture was purified by HPLC
  5. additiontreated with strong cation exchange column chromatography

Sources & evidence

ORD record
ord-a49ff06dec0a46b29633949e211856f4
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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