Acetic Acid → HCID 178515976, compound

HRID 1890696Notes

Reaction equation

HRID 1890696 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]2[CH:14]=[CH:15][C:16]3[N:17]([C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24](F)[N:23]=4)=[CH:20][N:21]=3)[N:18]=2)[CH:5]=[CH:6][CH:7]=1.C(O)(=[O:31])C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]2[CH:14]=[CH:15][C:16]3[N:17]([C:19]([C:22]4[N:23]=[C:24]([OH:31])[CH:25]=[CH:26][CH:27]=4)=[CH:20][N:21]=3)[N:18]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 58335579HCID 58335579, compound

Product 1

HCID 178515976HCID 178515976, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

In step 16-1, a suspension of (R)-6-(2-(3-fluorophenyl)pyrrolidin-1-yl)-3-(6-fluoropyridin-2-yl)imidazo[1,2-b]pyridazine (16 g, 42 mmol) in acetic acid (150 mL) was heated overnight at 120° C. (approx. 20 hours). The suspension turned clear after heating. The mixture was concentrated under vacuum to give a brown oil. The oil was dissolved in CH2Cl2 (750 mL) and washed with saturated NaHCO3 (300 mL×3), brine (300 mL×2). The organic layer was separated, dried over (Na2SO4) and concentrated to give 15.5 g of the crude (R)-6-(6-(2-(3-fluorophenyl)pyrrolidin-1-yl)imidazo[1,2-b]pyridazin-3-yl)pyridin-2-ol (16-1) which was used in the next step without further purification. LC/MS: 376.2 (M+H+).

Workup

  1. temperatureafter heating
  2. concentrationThe mixture was concentrated under vacuum
  3. customto give a brown oil
  4. washwashed with saturated NaHCO3 (300 mL×3), brine (300 mL×2)
  5. customThe organic layer was separated
  6. dry with materialdried over (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-88cedbbbfdb24c00a929800cd6512835
Source dataset
uspto-grants-2013_08
Patent number
US08507488B2

Reaction notes

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