Sodium Bicarbonate → HCID 178459263, compound

HRID 1483821Notes

Reaction equation

HRID 1483821 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=3)=[CH:9][N:10]=2)[N:7]=1.[NH2:18][C@H:19]1[CH2:24][CH2:23][C@H:22]([C:25]([OH:28])([CH3:27])[CH3:26])[CH2:21][CH2:20]1.C([O-])(O)=O.[Na+]>CN1C(=O)CCC1>[F:17][C:13]1[CH:12]=[C:11]([C:8]2[N:6]3[N:7]=[C:2]([NH:18][C@H:19]4[CH2:24][CH2:23][C@H:22]([C:25]([OH:28])([CH3:26])[CH3:27])[CH2:21][CH2:20]4)[CH:3]=[CH:4][C:5]3=[N:10][CH:9]=2)[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 59380310HCID 59380310, compoundHCID 178459266HCID 178459266, compound

Product 1

HCID 178459263HCID 178459263, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of give 6-chloro-3-(3-fluorophenyl)imidazo[1,2-b]pyridazine (100 mg, 0.404 mmol) in NMP (2 mL) was added 2-(trans-4-aminocyclohexyl)propan-2-ol (95 mg, 0.6 mmol) and NaHCO3 (101.8 mg, 1.21 mmol). The mixture was purged with nitrogen and kept at 180° C. for 30 min with M.W. reaction. LCMS showed the reaction was complete. The mixture was partitioned between water (100 mL) and EtOAc (50 mL). The aqueous layer was extracted with EtOAc (50 mL*3). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by prep. HPLC to give EX. 8-75 (10.6 mg, 7.2%) as a yellow solid.

Workup

  1. customThe mixture was purged with nitrogen
  2. customreaction
  3. customThe mixture was partitioned between water (100 mL) and EtOAc (50 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (50 mL*3)
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by prep
  9. customHPLC to give EX

Sources & evidence

ORD record
ord-42e566c3fd844cf7801c430761f36b58
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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