4-Nitrophenyl chloroformate → HCID 86670942, compound

HRID 515286Notes

Reaction equation

HRID 515286 reaction equation
[C:1](Cl)(=O)[O:2]C1C=CC([N+]([O-])=O)=CC=1.[NH2:14][C:15]1[CH:44]=[CH:43][C:18]([CH:19]=[C:20]2[CH2:25][CH2:24][N:23]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]([OH:42])([C:38]([F:41])([F:40])[F:39])[C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=3)[CH2:22][CH2:21]2)=[CH:17][CH:16]=1.[NH2:45][CH2:46][C:47]([CH3:50])([OH:49])[CH3:48]>O1CCOCC1>[F:37][C:34]([F:35])([F:36])[C:33]([C:30]1[CH:31]=[CH:32][C:27]([CH2:26][N:23]2[CH2:22][CH2:21][C:20](=[CH:19][C:18]3[CH:17]=[CH:16][C:15]([NH:14][C:1]([NH:45][CH2:46][C:47]([OH:49])([CH3:50])[CH3:48])=[O:2])=[CH:44][CH:43]=3)[CH2:25][CH2:24]2)=[CH:28][CH:29]=1)([OH:42])[C:38]([F:41])([F:39])[F:40]

Participants

5

Reactant 3

HCID 821294-Nitrophenyl chloroformateHCID 951022-Propanol, 1-amino-2-methyl-HCID 86670943HCID 86670943, compound

Product 1

HCID 86670942HCID 86670942, compoundYield 13.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-Nitrophenyl carbonochloridate (0.225 mmol, 45.4 mg) was added to a stirred solution of 2-(4-((4-(4-aminobenzylidene)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.225 mmol, 100 mg) in dioxane (1 mL) and the mixture stirred at room temperature for 1 hour. 1-Amino-2-methylpropan-2-ol (0.675 mmol, 60.2 mg) was added and the mixture stirred at room temperature for 1.5 hours. The mixture was washed with water (1 mL), the organic phase dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by HPLC and treated with strong cation exchange column to afford the title compound (17 mg). MS (ESI) m/z 560.2 [M+H]+

Workup

  1. stirringthe mixture stirred at room temperature for 1.5 hours
  2. washThe mixture was washed with water (1 mL)
  3. dry with materialthe organic phase dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by HPLC
  7. additiontreated with strong cation exchange column

Sources & evidence

ORD record
ord-4d75b1fb37564e87a14da3ec7ba3614c
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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