Sodium Hydroxide → HCID 58207979, compound

HRID 1958499Notes

Reaction equation

HRID 1958499 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[N:11]([CH:24]=[C:25]([C:27]([O:29]CC)=[O:28])[N:26]=2)[CH:12]=[C:13]([C:15]2[S:19][C:18]([CH2:20][CH:21]([CH3:23])[CH3:22])=[N:17][CH:16]=2)[CH:14]=1.[OH-].[Na+]>CO.C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[N:11]([CH:24]=[C:25]([C:27]([OH:29])=[O:28])[N:26]=2)[CH:12]=[C:13]([C:15]2[S:19][C:18]([CH2:20][CH:21]([CH3:23])[CH3:22])=[N:17][CH:16]=2)[CH:14]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58207999HCID 58207999, compound

Product 1

HCID 58207979HCID 58207979, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 8-(2,4-difluorophenyl)-6-(2-isobutylthiazol-5-yl)imidazo[1,2-a]pyridine-2-carboxylate (47.7 mg, 0.108 mmol) in MeOH (2 mL) and THF (2 mL) was added 1N NaOH (2 mL). The mixture was stirred at room temperature overnight. The mixture was concentrated, diluted with EtOAc (10 mL), washed with water (5 mL) and concentrated. The residue was purified by prep HPLC to give a white solid as a TFA salt form (32 mg, 56% yield). LCMS (Conditions C): Tr 3.55 min; (M+H)+=414.29 (100%), 415.37 (20%), 416.26 (10%). 1H NMR, 400 MHz, CDCl3: 8.37 (d, J=1.5 Hz, 1H), 8.33 (s, 1H), 7.92 (s, 1H), 7.88 (m, 1H), 7.61 (s, 1H), 7.13-7.03 (m, 2H), 2.96 (d, J=7.1 Hz, 2H), 2.18 (m, 1H), 1.06 (d, J=6.6 Hz, 6H).

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with EtOAc (10 mL)
  3. washwashed with water (5 mL)
  4. concentrationconcentrated
  5. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-a0da6b6894cf42cb9ce143b17ba58ca4
Source dataset
uspto-grants-2013_04
Patent number
US08410128B2

Reaction notes

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