Hydrogen Peroxide → HCID 25127164, compound

HRID 558159Notes

Reaction equation

HRID 558159 reaction equation
OO.[N:3]1([CH2:8][CH2:9][NH:10][C:11]2[N:16]=[C:15]([C:17]3[S:21][C:20]4[C:22]([C:26]5[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=5[C:33]([CH3:37])([CH3:36])[C:34]#[N:35])=[CH:23][CH:24]=[CH:25][C:19]=4[CH:18]=3)[C:14]([F:38])=[CH:13][N:12]=2)[CH:7]=[CH:6][N:5]=[N:4]1.[O:39]1CCOCCOCCOCCOCCOCC1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O>[N:3]1([CH2:8][CH2:9][NH:10][C:11]2[N:16]=[C:15]([C:17]3[S:21][C:20]4[C:22]([C:26]5[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=5[C:33]([CH3:36])([CH3:37])[C:34]([NH2:35])=[O:39])=[CH:23][CH:24]=[CH:25][C:19]=4[CH:18]=3)[C:14]([F:38])=[CH:13][N:12]=2)[CH:7]=[CH:6][N:5]=[N:4]1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 2855718-Crown-6HCID 25126511HCID 25126511, compound

Product 1

HCID 25127164HCID 25127164, compoundYield 399.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Add hydrogen peroxide to a stirred solution of 2-(2-(2-(2-(2-(1H-1,2,3-triazol-1-yl)ethylamino)-5-fluoropyrimidin-4-yl)benzo[b]thiophen-7-yl)-4-fluorophenyl)-2-methylpropanenitrile (140 mg, 279 μmol), 1,4,7,10,13,16-hexaoxacyclooctadecane (14 mg, 1% wt), and sodium carbonate (1 M, 5 mL, 5 mmol) in 10 mL ethanol drop wise. Stir the mixture at RT for 48 h. Dilute the reaction mixture with water and extract with DCM. Dry the organic phase over sodium sulfate and concentrate in vacuo. Purify the crude product by FCC (10% methanol in DCM as elute) to give the title compound as a yellow solid (110 mg, 76%). MS (ES) m/z 520 [M+1]+.

Workup

  1. extractionextract with DCM
  2. dry with materialDry the organic phase over sodium sulfate
  3. concentrationconcentrate in vacuo
  4. customPurify the crude product
  5. washby FCC (10% methanol in DCM as elute)

Sources & evidence

ORD record
ord-56ac2bbe18434c2d854ec55d128570d0
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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