3-(2,6-Dichloro-4-pyridinyl)-5-methoxy-1H-pyrrolo[2,3-b]pyridine → HCID 178493709, compound

HRID 2089019

Reaction equation

HRID 2089019 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=3)[NH:10][CH:9]=2)[CH:5]=[C:4]([Cl:19])[N:3]=1.[NH2:20][C@H:21]1[CH2:26][CH2:25][C@H:24]([OH:27])[CH2:23][CH2:22]1>C(#N)C.CCO>[Cl:19][C:4]1[N:3]=[C:2]([NH:20][C@H:21]2[CH2:26][CH2:25][C@H:24]([OH:27])[CH2:23][CH2:22]2)[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=3)[NH:10][CH:9]=2)[CH:5]=1

Participants

5

Reactant 2

HCID 871921833-(2,6-Dichloro-4-pyridinyl)-5-methoxy-1H-pyrrolo[2,3-b]pyridineHCID 178511715HCID 178511715, compound

Product 1

HCID 178493709HCID 178493709, compoundYield 40.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of Example 149e (43.9 mg, 0.146 mmol) and trans-4-aminocyclohexanol (0.337 g, 2.92 mmol) in acetonitrile (1.5 mL) and EtOH (1.5 mL) was heated at 190° C. for 3 hours in a Biotage microwave reactor. The solvent was evaporated. The residue was treated with 5% citric acid and brine, and extracted with EtOAc (2×). The combined organic layers were dried over MgSO4, filtered, concentrated, and purified on a 12 g column using the ISCO Companion flash system eluting with CH2Cl2/EtOAc (5:95) to 100% EtOAc to give 22.0 mg of the title compound. 1H NMR (500 MHz, DMSO-d6) ppm 1.15-1.33 (m, 3H), 1.84 (d, J=10.98 Hz, 2H), 1.96 (d, J=11.29 Hz, 2H), 2.07 (m, 1H), 3.40 (m, 1H), 3.59 (m, 1H), 3.89 (s, 3H), 6.76-6.90 (m, 2H), 7.78 (d, J=2.75 Hz, 1H), 8.07 (dd, J=6.71, 2.75 Hz, 2H), 12.03 (s, 1H). MS (APCI+) m/z 373.4 (M+H)+.

Workup

  1. customThe solvent was evaporated
  2. additionThe residue was treated with 5% citric acid and brine
  3. extractionextracted with EtOAc (2×)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified on a 12 g column
  8. washeluting with CH2Cl2/EtOAc (5:95) to 100% EtOAc

Sources & evidence

ORD record
ord-da62706941194e16b5f98557cbc4d4a6
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Linked notes

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