Chloride → HCID 24821338, compound

HRID 1028472Notes

Reaction equation

HRID 1028472 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([O:7][C:8]2[S:9][C:10]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]([NH2:21])[CH3:20])=[CH:15][CH:14]=3)=[CH:11][N:12]=2)=[CH:5][CH:4]=1.[Cl-].ClC(Cl)(Cl)[C:27]([N:29]=C=O)=[O:28].C([O-])([O-])=O.[Na+].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([O:7][C:8]2[S:9][C:10]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]([NH:21][C:27]([NH2:29])=[O:28])[CH3:20])=[CH:15][CH:14]=3)=[CH:11][N:12]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 312ChlorideHCID 10340Sodium CarbonateHCID 76400Trichloroacetyl isocyanateHCID 69189942HCID 69189942, compound

Product 1

HCID 24821338HCID 24821338, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Example 11D ((110 mg, 0.337 mmol) in methylenie chloride (1 mL) cooled to 0° C. was added trichloroacetyl isocyanate (50 μL, 0.42 mmol, 1.2 eq.). The mixture was stirred at 0° C. for 10 minutes and then methanol (10 mL) and a catalytic amount of Na2CO3 were added. The mixture was stirred at room temperature for 5 hours. The reaction was then concentrated. The reaction mixture was purified on silica gel eluting with ethyl acetate:hexane gradient (0-80%) to give the title compound (42 mg, 34%). 1H NMR (300 MHz, DMSO-d6) δ ppm 7.66 (s, 1 H), 7.45-7.53 (m, 2 H), 7.32-7.40 (m, 2 H), 7.28-7.31 (m, 2 H), 7.02-7.06 (m, 2 H), 6.44 (d, J=8.09 Hz, 1 H), 5.42 (s, 2 H), 4.59-4.77 (m, 1 H), 3.79 (s, 3 H), 1.29 (d, J=6.99 Hz, 3 H); MS (DCI) m/z 370 (M+H).

Workup

  1. stirringThe mixture was stirred at room temperature for 5 hours
  2. concentrationThe reaction was then concentrated
  3. customThe reaction mixture was purified on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-2157389bbb474fb9ae5f1cf813633637
Source dataset
uspto-grants-2014_05
Patent number
US08735595B2

Reaction notes

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