Water → HCID 59175838, compound

HRID 1807785Notes

Reaction equation

HRID 1807785 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]([S:21]([N:24]2[CH2:29][CH2:28][N:27]([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([C:37]([OH:46])([C:42]([F:45])([F:44])[F:43])[C:38]([F:41])([F:40])[F:39])=[CH:33][CH:32]=3)[CH2:26][CH2:25]2)(=[O:23])=[O:22])=[CH:17][CH:16]=1.[CH:47]1([CH:50]([NH2:52])C)[CH2:49][CH2:48]1.O>ClCCl>[CH:47]1([CH2:50][NH:52][C:1]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([S:21]([N:24]3[CH2:25][CH2:26][N:27]([CH2:30][C:31]4[CH:32]=[CH:33][C:34]([C:37]([OH:46])([C:38]([F:39])([F:40])[F:41])[C:42]([F:45])([F:44])[F:43])=[CH:35][CH:36]=4)[CH2:28][CH2:29]3)(=[O:22])=[O:23])=[CH:19][CH:20]=2)=[O:2])[CH2:49][CH2:48]1

Participants

6

Reactant 4

HCID 962WaterHCID 821294-Nitrophenyl chloroformateHCID 5192391-CyclopropylethanamineHCID 86638574HCID 86638574, compound

Product 1

HCID 59175838HCID 59175838, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Nitrophenyl carbonochloridate (0.126 mmol, 0.02549 g) was added to a stirred solution of 2-(4-((4-(4-aminophenylsulfonyl)piperazin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.126 mmol, 0.0629 g) in dichloromethane (1 mL). After 1 hour, cyclopropylethanamine (0.380 mmol, 0.027 g) was added and stirring was continued for 1 hour. Water (5 mL) was added and the organic layer was separated, washed with water (3×10 mL), dried over magnesium sulphate and concentrated under reduced pressure to give a yellow gum. Purification was achieved by preparative HPLC, giving after filtration through a silica carbonate column in methanol, the title compound as a pale gum (15.2 mg). MS (ESI) m/z 595.0 [M+H]+

Workup

  1. waitwas continued for 1 hour
  2. customthe organic layer was separated
  3. washwashed with water (3×10 mL)
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow gum
  7. customPurification
  8. customgiving
  9. filtrationafter filtration through a silica carbonate column in methanol

Sources & evidence

ORD record
ord-3c8c4a2519ac494e906a314649056730
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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