Sodium Hydroxide → HCID 57929974, compound

HRID 1930001Notes

Reaction equation

HRID 1930001 reaction equation
C([O:4][CH2:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[S:15][C:16]([C:28]3[CH:29]=[CH:30][C:31]4[N:32]([C:34]([CH:37]([CH3:39])[CH3:38])=[N:35][N:36]=4)[N:33]=3)=[C:17]([C:19]3[CH:24]=[C:23]([F:25])[C:22]([F:26])=[CH:21][C:20]=3[F:27])[N:18]=2)[CH2:10][CH2:9]1)=[O:7])(=O)C.[OH-].[Na+]>C1COCC1.O>[OH:4][CH2:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[S:15][C:16]([C:28]3[CH:29]=[CH:30][C:31]4[N:32]([C:34]([CH:37]([CH3:39])[CH3:38])=[N:35][N:36]=4)[N:33]=3)=[C:17]([C:19]3[CH:24]=[C:23]([F:25])[C:22]([F:26])=[CH:21][C:20]=3[F:27])[N:18]=2)[CH2:12][CH2:13]1)=[O:7]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57929929HCID 57929929, compound

Product 1

HCID 57929974HCID 57929974, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A round-bottomed flask equipped with rubber septum and nitrogen inlet needle was charged with 2-(4-(5-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-4-(2,4,5-trifluorophenyl)thiazol-2-yl)piperidin-1-yl)-2-oxoethyl acetate (0.22 g, 0.39 mmol, prepared using General Procedure Q.1 from Preparation #O.1.1.1 with TFA, General Procedure T.1 with acetoxyacetyl chloride) in THF (5.0 mL). A 1.0 M aqueous NaOH solution (2 mL, 2 mmol) was added. The reaction mixture was stirred at about 40° C. for about 1 h. The reaction was diluted with water and then extracted with EtOAc (2×100 mL). The combined organic layers were washed with water, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by RP-HPLC (Table 1, Method f) to give the title compound (0.145 g, 71%): LC/MS (Table 1, Method a) Rt=2.89 min; MS m/z: 518.1 (M+H)+.

Workup

  1. customA round-bottomed flask equipped with rubber septum and nitrogen inlet needle
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by RP-HPLC (Table 1, Method f)

Sources & evidence

ORD record
ord-43ad06891af54dc9a27fb10be64d24d0
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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