3-Furanol, tetrahydro- → HCID 67003577, compound

HRID 2362684Notes

Reaction equation

HRID 2362684 reaction equation
[Cl:1][C:2]1[C:3]([C:28]2[S:32][C:31]([C:33]3([O:37][CH2:38][O:39][CH3:40])[CH2:36][CH2:35][CH2:34]3)=[N:30][CH:29]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)[N:8]([S:18]([C:21]3[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[C:5]2=[N:6][CH:7]=1.[O:41]1[CH2:45][CH2:44][CH:43](O)[CH2:42]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([C:28]2[S:32][C:31]([C:33]3([O:37][CH2:38][O:39][CH3:40])[CH2:36][CH2:35][CH2:34]3)=[N:30][CH:29]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH:43]4[CH2:44][CH2:45][O:41][CH2:42]4)=[CH:13][CH:12]=3)[N:8]([S:18]([C:21]3[CH:22]=[CH:23][C:24]([CH3:25])=[CH:26][CH:27]=3)(=[O:19])=[O:20])[C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 99603-Furanol, tetrahydro-2×HCID 11776Triphenylphosphine2×HCID 75555Diisopropyl diazene-1,2-dicarboxylate2×HCID 67003716HCID 67003716, compound

Product 1

HCID 67003577HCID 67003577, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(5-chloro-4-(2-(1-(methoxymethoxy)cyclobutyl)thiazol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-2-yl)phenol (Example 69A) (60 mg, 0.101 mmol), tetrahydrofuran-3-ol (12 mg, 0.131 mmol), and triphenylphosphine (34.3 mg, 0.131 mmol) in anhydrous tetrahydrofuran (1 mL) was treated with diisopropyl azodicarboxylate (0.025 mL, 0.131 mmol). The reaction was stirred for 16 hours at ambient temperature. The reaction treated with more tetrahydrofuran-3-ol (12 mg, 0.131 mmol), diisopropyl azodicarboxylate (0.025 mL, 0.131 mmol) and triphenylphosphine (34.3 mg, 0.131 mmol), and the reaction was warmed to 70° C. for 5 hours. The reaction was cooled, diluted with ethyl acetate, and washed with water and brine. The organic layer dried with sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 30 to 40% ethyl acetate in hexanes, to give the title compound. MS ESI(+) m/z 666.1 [M+H]+.

Workup

  1. temperaturethe reaction was warmed to 70° C. for 5 hours
  2. temperatureThe reaction was cooled
  3. washwashed with water and brine
  4. dry with materialThe organic layer dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel
  8. washeluting with a gradient of 30 to 40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-847ffa8ba47643619244d939590e906e
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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