Sodium Hydroxide → HCID 58207979, compound

HRID 2197572Notes

Reaction equation

HRID 2197572 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-736fdd058e7242a892aabeb63b25c923
Source dataset
uspto-grants-2012_12
Patent number
US08338604B2

Reaction notes

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