Potassium Iodide → HCID 66977300, compound

HRID 712330Notes

Reaction equation

HRID 712330 reaction equation
[CH2:1]([C:3]1([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:8][CH2:7][N:6]([C:9]2[N:14]=[CH:13][C:12]([C:15]3[CH:16]=[C:17]([C:34]#[C:35][CH2:36][O:37]S(C)(=O)=O)[C:18]4[S:22][C:21]([N:23]5[CH2:28][N:27]([CH3:29])[CH2:26][N:25]([CH2:30][CH3:31])[C:24]5=[O:32])=[N:20][C:19]=4[CH:33]=3)=[CH:11][N:10]=2)[CH2:5][CH2:4]1)[CH3:2].O[N:48]1[C:52](=[O:53])[C:51]2=[CH:54][CH:55]=[CH:56][CH:57]=[C:50]2[C:49]1=[O:58].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[O:58]=[C:49]1[C:50]2[C:51](=[CH:54][CH:55]=[CH:56][CH:57]=2)[C:52](=[O:53])[N:48]1[O:37][CH2:36][C:35]#[C:34][C:17]1[C:18]2[S:22][C:21]([N:23]3[CH2:28][N:27]([CH3:29])[CH2:26][N:25]([CH2:30][CH3:31])[C:24]3=[O:32])=[N:20][C:19]=2[CH:33]=[C:15]([C:12]2[CH:11]=[N:10][C:9]([N:6]3[CH2:5][CH2:4][C:3]([CH2:1][CH3:2])([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:8][CH2:7]3)=[N:14][CH:13]=2)[CH:16]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10665N-HydroxyphthalimideHCID 11430Potassium CarbonateHCID 86664040HCID 86664040, compound

Product 1

HCID 66977300HCID 66977300, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 4-ethyl-1-[5-[2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-7-(3-methylsulfonyloxyprop-1-ynyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylate (368 mg, 0.55 mmol), N-hydroxyphthalimide (134 mg, 0.82 mmol), potassium iodide (9 mg, 0.05 mmol) and potassium carbonate (152 mg, 1.10 mmol) were dissolved in anhydrous DMF (5 mL) under argon and heated to 60° C. for 3 h. The cooled mixture was diluted with water, extracted into EtOAc (4×30 mL) and the organic phase washed with water then brine, dried over Na2SO4 and concentrated to dryness under reduced pressure. A yellow solid was obtained and the mixture was purified by chromatography, Biotage SP4, 40 g Si cartridge, 50-80% EtOAc in cyclohexane. The relevant fractions were combined to give the desired compound as a pale yellow oil, 233 mg (58%). MS: 737.13 [M+H]+.

Workup

  1. extractionextracted into EtOAc (4×30 mL)
  2. washthe organic phase washed with water
  3. dry with materialbrine, dried over Na2SO4
  4. concentrationconcentrated to dryness under reduced pressure
  5. customA yellow solid was obtained
  6. customthe mixture was purified by chromatography, Biotage SP4, 40 g Si cartridge, 50-80% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-61731bfcff484374884b7bb7eee857b2
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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