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Hydrochloric Acid → 3-(5-((1R,2S)-1-(4H-Benzo[d][1,3]dioxin-7-yl)-2-(2,2-difluoropropanamido)propoxy)-1H-indazol-1-yl)benzoic acid

HRID 1406587
Notes
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Reaction equation

HRID 1406587 reaction equation
[O:1]1[C:6]2[CH:7]=[C:8]([C@@H:11]([O:21][C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[N:27]([C:31]3[CH:32]=[C:33]([CH:41]=[CH:42][CH:43]=3)[C:34]([O:36]CC(C)C)=[O:35])[N:26]=[CH:25]4)[C@@H:12]([NH:14][C:15](=[O:20])[C:16]([F:19])([F:18])[CH3:17])[CH3:13])[CH:9]=[CH:10][C:5]=2[CH2:4][O:3][CH2:2]1.[OH-].[Li+].C(OCC)(=O)C.Cl>CO.C1COCC1.O>[O:1]1[C:6]2[CH:7]=[C:8]([C@@H:11]([O:21][C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[N:27]([C:31]3[CH:32]=[C:33]([CH:41]=[CH:42][CH:43]=3)[C:34]([OH:36])=[O:35])[N:26]=[CH:25]4)[C@@H:12]([NH:14][C:15](=[O:20])[C:16]([F:19])([F:18])[CH3:17])[CH3:13])[CH:9]=[CH:10][C:5]=2[CH2:4][O:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 59272926Isobutyl 3-(5-((1R,2S)-1-(4H-benzo[d][1,3]dioxin-7-yl)-2-(2,2-difluoropropanamido)propoxy)-1H-indazol-1-yl)benzoate

Product 1

HCID 685799603-(5-((1R,2S)-1-(4H-Benzo[d][1,3]dioxin-7-yl)-2-(2,2-difluoropropanamido)propoxy)-1H-indazol-1-yl)benzoic acid
Yield 100.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Isobutyl 3-(5-((1R,2S)-1-(4H-benzo[d][1,3]dioxin-7-yl)-2-(2,2-difluoropropanamido)propoxy)-1H-indazol-1-yl)benzoate (I5a) (398 mg, 0.67 mmol) was dissolved in methanol (3 mL) and THF (3.0 mL). Lithium hydroxide (0.032 mL, 2.01 mmol) dissolved in water (2.5 mL) was added. A clear slightly pink solution was obtained. After 2 h the solution was ice-cold. Ethyl acetate was added and then hydrochloric acid (1M) to acidic pH. The water phase was once more extracted with ethyl acetate. The collected organic phases were dried over magnesium sulfate and evaporated. It was dissolved in methanol and the solution was applied onto a 1 g SCX column. The methanol eluate (ca 15 mL) was concentrated. Freeze-drying from acetonitrile/water gave the title compound (362 mg, 100%).

Workup

  1. additionwas added
  2. customA clear slightly pink solution was obtained
  3. extractionThe water phase was once more extracted with ethyl acetate
  4. dry with materialThe collected organic phases were dried over magnesium sulfate
  5. customevaporated
  6. dissolutionIt was dissolved in methanol
  7. concentrationThe methanol eluate (ca 15 mL) was concentrated
  8. dry with materialFreeze-drying from acetonitrile/water

Sources & evidence

ORD record
ord-948557bdcd854360874a2305ac01b005
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08916600B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes