Citric Acid → HCID 70817834, compound

HRID 1501356Notes

Reaction equation

HRID 1501356 reaction equation
[NH2:1][C:2]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:13]=[C:14]4[CH:19]=[CH:18][C:17]([C:20]([O:22]CC)=[O:21])=[N:16][N:15]4[C:25]=3[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3]1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[NH2:1][C:2]1([C:6]2[CH:7]=[CH:8][C:9]([C:12]3[N:13]=[C:14]4[CH:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[N:16][N:15]4[C:25]=3[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:10][CH:11]=2)[CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 70818063HCID 70818063, compound

Product 1

HCID 70817834HCID 70817834, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-b]pyridazine-6-carboxylate that was prepared in a manner analgous to that described for Example 4 (260 mg, 0.63 mmol) in methanol (1.5 mL) was added aqueous sodium hydroxide (3N, 0.63 mL, 1.89 mmol, 3.0 eq), and the resulting mixture was stirred at 50° C. for 1 h. The resulting mixture was added to ice water, made slightly acidic with aqueous citric acid (10%), and washed with DCM (3×25 mL). The aqueous phase was made alkaline and adjusted to pH4 using hydrochloric acid (1N). The precipitate was collected by filtration, washed with water and dried under high vacuum overnight to yield 218 mg (88% yield) of the title compound.

Workup

  1. washwashed with DCM (3×25 mL)
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-83633d67c78649248a4ddc130b825105
Source dataset
uspto-grants-2015_12
Patent number
US09206185B2

Reaction notes

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