Triethylamine → HCID 49787496, compound

HRID 1966047Notes

Reaction equation

HRID 1966047 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:23]=[C:24]([CH3:26])[CH:25]=1)[O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=1[S:14]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)(=[O:16])=[O:15].[F:27][C:28]([F:40])([F:39])[C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:26][C:24]1[CH:23]=[C:4]([CH:3]=[C:2]([CH3:1])[CH:25]=1)[O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=1[S:14]([N:17]1[CH2:22][CH2:21][N:20]([S:35]([C:32]2[CH:31]=[CH:30][C:29]([C:28]([F:27])([F:39])[F:40])=[CH:34][CH:33]=2)(=[O:37])=[O:36])[CH2:19][CH2:18]1)(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 10133817HCID 10133817, compound

Product 1

HCID 49787496HCID 49787496, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 24 (0.099 g, 0.27 mmol) in CH2Cl2 (3 mL) was added 4-(trifluoromethyl)benzenesulfonyl chloride (0.093 g, 0.38 mmol) and triethylamine (0.039 g, 0.38 mmol). The reaction mixture was stirred for 18 hrs, whereupon the starting material was consumed (TLC, 1% MeOH in CH2Cl2). The reaction mixture was then concentrated in vacuo, redissolved in a minimal amount of CH2Cl2, and chromatographed over normal phase silica (MeOH/CH2Cl2). The fractions containing the desired product were combined and concentrated in vacuo to yield a white solid. The solid was triturated with diisopropyl ether/hexanes and vacuum filtered to afford compound 60 as a white powder. (0.065 g, 42.2% yield, 95.7% HPLC purity). 1H NMR (500 MHz, CDCl3): 8.23 (d, J=2 Hz, 1H), 7.86 (m, 4H), 7.67 (dd, J1=9 Hz, J2=2 Hz, 1H), 6.95 (s, 1H), 6.89 (d, J=9 Hz, 1H), 6.68 (s, 2H), 3.48 (m, 4H), 3.15 (m, 4H), 2.35 (s, 6H); MS (ESI, EI+): m/z=580 (MH+).

Workup

  1. customwas consumed (TLC, 1% MeOH in CH2Cl2)
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. dissolutionredissolved in a minimal amount of CH2Cl2
  4. customchromatographed over normal phase silica (MeOH/CH2Cl2)
  5. additionThe fractions containing the desired product
  6. concentrationconcentrated in vacuo
  7. customto yield a white solid
  8. customThe solid was triturated with diisopropyl ether/hexanes and vacuum
  9. filtrationfiltered

Sources & evidence

ORD record
ord-b9e07e839d9a4d10bb82f3b0837a4c33
Source dataset
uspto-grants-2013_04
Patent number
US08420639B2

Reaction notes

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