Morpholine → HCID 59278145, compound

HRID 559683Notes

Reaction equation

HRID 559683 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-2be7cb93b0cb48d8a51713589deb3ca7
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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