Lithium Hydroxide → 3-(1-(3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)cyclopropylamino)propanoic acid

HRID 1177463Notes

Reaction equation

HRID 1177463 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:26]2([NH:29][CH2:30][CH2:31][C:32]([O:34]C)=[O:33])[CH2:28][CH2:27]2)[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2.[OH-].[Li+]>O1CCCC1.CO>[F:1][C:2]1[CH:3]=[C:4]([C:26]2([NH:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])[CH2:27][CH2:28]2)[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68635658Methyl 3-(1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)cyclopropylamino)propanoate

Product 1

HCID 446011073-(1-(3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)cyclopropylamino)propanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-(1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)cyclopropylamino)propanoate (0.031 g, 0.064 mmol) in tetrahydrofuran (0.2 mL) and methanol (0.1 mL) was added 1 M lithium hydroxide solution (0.19 mL, 0.19 mmol) and stirred at room temperature for 3 hours. The reaction mixture was concentrated in vacuo and the resulting slurry was diluted with water and neutralized (to pH=˜7) with aqueous 1 N HCl solution. The aqueous suspension was extracted with 15% MeOH/CHCl3; the organic extracts were combined, dried (K2CO3), filtered, and concentrated in vacuo. Purification via reverse phase prep. HPLC afforded the title compound as an off-white amorphous solid. MS (ESI) m/z: Calculated: 473.2; Observed: 474.1 (M++1).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe resulting slurry was diluted with water and neutralized (to pH=˜7) with aqueous 1 N HCl solution
  3. extractionThe aqueous suspension was extracted with 15% MeOH/CHCl3
  4. dry with materialdried (K2CO3)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification via reverse phase prep

Sources & evidence

ORD record
ord-bc7c94f073bb4d34a572a0663e2b0f71
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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