Morpholine → HCID 59278145, compound

HRID 2198152Notes

Reaction equation

HRID 2198152 reaction equation
Br[C:2]1[S:3][C:4]([CH2:7][NH:8][C:9]([C:11]2[C:12]3[CH:19]=[N:18][N:17]([C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)[C:13]=3[CH:14]=[N:15][CH:16]=2)=[O:10])=[CH:5][N:6]=1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>>[N:27]1([C:2]2[S:3][C:4]([CH2:7][NH:8][C:9]([C:11]3[C:12]4[CH:19]=[N:18][N:17]([C:20]5[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=5)[C:13]=4[CH:14]=[N:15][CH:16]=3)=[O:10])=[CH:5][N:6]=2)[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 59278116HCID 59278116, compound

Product 1

HCID 59278145HCID 59278145, compound

Procedure

A solution of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid (2-bromo-thiazol-5-ylmethyl)-amide (80 mg, 0.21 mmol) in morpholine (2 mL) was heated at 140° C. for 72 hours in a sealed tube. The mixture was partitioned between EtOAc (20 mL) and saturated aqueous ammonium chloride (20 mL). The organic layer was separated and washed with brine (20 mL), dried over sodium sulfate, filtered and concentrated. The crude material was purified by silica gel chromatography eluting with a gradient of 0-10% methanol in dichloromethane. The purification was repeated using the same conditions listed above. The material from the purification was diluted with dichloromethane (1 mL) followed by hexanes (5 mL) and filtered to afford the title compound.

Workup

  1. customThe mixture was partitioned between EtOAc (20 mL) and saturated aqueous ammonium chloride (20 mL)
  2. customThe organic layer was separated
  3. washwashed with brine (20 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by silica gel chromatography
  8. washeluting with a gradient of 0-10% methanol in dichloromethane
  9. customThe purification
  10. customThe material from the purification
  11. additionwas diluted with dichloromethane (1 mL)
  12. filtrationfiltered

Sources & evidence

ORD record
ord-9126fcd1e89a410d8c143acabe8a8a0e
Source dataset
uspto-grants-2012_12
Patent number
US08338610B2

Reaction notes

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