Pyridine → HCID 57985932, compound

HRID 1869218Notes

Reaction equation

HRID 1869218 reaction equation
[CH:1]1([CH:7]([C:18]2[C:26]3[C:21](=[N:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=2)[CH:8]2[C:13](=O)[O:12]C(C)(C)OC2=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:27]1C=CC=C[CH:28]=1.CN>O>[CH:1]1([CH:7]([C:18]2[C:26]3[C:21](=[N:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=2)[CH2:8][C:13]([NH:27][CH3:28])=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6329MethylamineHCID 57985904HCID 57985904, compound

Product 1

HCID 57985932HCID 57985932, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-[cyclohexyl-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-2,2-dimethyl-[1,3]dioxane-4,6-dione (560 mg, 1.57 mmol), pyridine (8 mL) and MeNH2 (2 M in THF, 16 mL) heated to 120° C. in sealed vial for 3 h. The reaction was cooled to RT and poured into water. The pH was adjusted to 7. And the resulting solution was extracted 5 times with EtOAc (100 mL) and 3 times with DCM (200 mL). The organic layers were combined, dried over MgSO4, filtered and concentrated, affording crude 3-Cyclohexyl-N-methyl-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propionamide (270 mg), which was used in the next step without purification.

Workup

  1. temperatureThe reaction was cooled to RT
  2. extractionAnd the resulting solution was extracted 5 times with EtOAc (100 mL) and 3 times with DCM (200 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-86779dab0cd64ba5a4d7f086e8dda1ab
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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