1,4-Dioxane → HCID 178479571, compound

HRID 1952377Notes

Reaction equation

HRID 1952377 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]2[NH:8][N:9]=[C:10]([CH2:11][N:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[C:14]([O:22][C:23]4[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=4)[C:13]3=[O:31])[C:5]2=[CH:4][CH:3]=1.O1CCOCC1>CO.C(Cl)Cl.Cl>[Cl-:29].[Cl:29][C:27]1[CH:28]=[C:23]([CH:24]=[C:25]([Cl:30])[CH:26]=1)[O:22][C:14]1[C:13](=[O:31])[N:12]([CH2:11][C:10]2[C:5]3[C:6](=[N:7][C:2]([NH3+:1])=[CH:3][CH:4]=3)[NH:8][N:9]=2)[CH:17]=[CH:16][C:15]=1[C:18]([F:19])([F:20])[F:21]

Participants

6

Reactant 2

HCID 312751,4-DioxaneHCID 178507302HCID 178507302, compound

Product 1

HCID 178479571HCID 178479571, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

1-[(6-amino-1H-pyrazolo[3,4-b]pyridin-3-yl)methyl]-3-(3,5-dichlorophenoxy)-4-(trifluoromethyl)pyridin-2(1H)-one (0.495 g, 1.05 mmol) was dissolved in a mixture of 20% methanol in CH2Cl2 (25 mL) and 4M HCl in dioxane (0.077 g, 2.10 mmol) was added. After 15 minutes, the reaction mixture was concentrated under reduced pressure and placed under vacuum for 4 hours to afford the title compound as a solid. 1H NMR (DMSO-d6 with NH4OH) δ 7.93 (d, J=7.1 Hz, 1H), 7.58 (d, J=8.7 Hz, 1H), 7.13-7.11 (m, 1H), 7.06-7.04 (m, 2H), 6.59 (d, J=7.2 Hz, 1H), 6.37-6.34 (m, 2H), 6.31 (d, J=8.7 Hz, 1H), 5.34 (s, 2H). HRMS (M+1)=470.0392.

Workup

  1. additionwas added
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. waitplaced under vacuum for 4 hours

Sources & evidence

ORD record
ord-36d5b30b410b4db98daea0f3818cabde
Source dataset
uspto-grants-2013_03
Patent number
US08404856B2

Reaction notes

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