Hydrochloric Acid → HCID 68292407, compound

HRID 1507952Notes

Reaction equation

HRID 1507952 reaction equation
C[O:2][C:3](=[O:30])[C:4]([CH3:29])([CH3:28])[C@H:5]([NH:7][C:8]1[C:9]2[N:10]([CH:17]=[C:18]([C:20]3[CH:21]=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)[CH:19]=2)[N:11]=[CH:12][C:13]=1[C:14](=[O:16])[NH2:15])[CH3:6].[OH-].[K+].Cl>CO.O>[C:14]([C:13]1[CH:12]=[N:11][N:10]2[CH:17]=[C:18]([C:20]3[CH:21]=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)[CH:19]=[C:9]2[C:8]=1[NH:7][C@H:5]([CH3:6])[C:4]([CH3:29])([CH3:28])[C:3]([OH:30])=[O:2])(=[O:16])[NH2:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 68292325HCID 68292325, compound

Product 1

HCID 68292407HCID 68292407, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(R)-methyl-3-((3-carbamoyl-6-(6-methoxypyridin-3-yl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-2,2-dimethylbutanoate (125 mg, 0.304 mmol) was dissolved in MeOH (25 mL) and water (1.0 mL). Potassium hydroxide (256 mg, 4.56 mmol) was added and the reaction mixture was heated at reflux overnight. After completion, the reaction mixture was cooled to room temperature and MeOH was removed under reduced pressure. The crude mass obtained was acidified to pH 5 at 0° C. using 1.5N HCl and stirred at room temperature for 15 minutes to give a solid that was collected by vacuum filtration and dried to afford the title compound (100 mg, 0.252 mmol, 83% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 1.13-1.15 (d, J=8.4 Hz, 6H), 1.25-1.26 (d, J=6.4 Hz, 3H), 3.86 (s, 3H), 4.68 (m, 1H), 6.84-6.86 (d, J=8.4 Hz, 1H), 7.25 (s, 1H), 8.06-8.064 (d, J=2 Hz, 1H), 8.15-8.18 (d, J=12 Hz, 2H), 8.59 (s, 1H), 10.86-10.89 (d, J=10 Hz, 1H). [α]24.8=1.6 (c=0.1, MeOH)

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux overnight
  3. customMeOH was removed under reduced pressure
  4. customThe crude mass obtained
  5. customwas acidified to pH 5 at 0° C.
  6. customto give a solid
  7. filtrationthat was collected by vacuum filtration
  8. customdried

Sources & evidence

ORD record
ord-04d2b1e5a1634dc9ba7902b077f76e24
Source dataset
uspto-grants-2015_12
Patent number
US09221826B2

Reaction notes

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