Sodium Hydroxide → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-1H-pyrazolo[4,3-b]pyridin-6-yl)benzo[d]thiazol-6-yl)ethanol

HRID 510285Notes

Reaction equation

HRID 510285 reaction equation
C([O:7][CH2:8][C@@H:9]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[C:10]1[C:28]([CH3:29])=[CH:27][C:13]2[N:14]=[C:15]([C:17]3[CH:18]=[C:19]4[N:25]([CH3:26])[N:24]=[CH:23][C:20]4=[N:21][CH:22]=3)[S:16][C:12]=2[C:11]=1[C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)(=O)C(C)(C)C.[OH-].[Na+]>C1COCC1.CO>[C:38]([O:37][C@@H:9]([C:10]1[C:28]([CH3:29])=[CH:27][C:13]2[N:14]=[C:15]([C:17]3[CH:18]=[C:19]4[N:25]([CH3:26])[N:24]=[CH:23][C:20]4=[N:21][CH:22]=3)[S:16][C:12]=2[C:11]=1[C:30]1[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=1)[CH2:8][OH:7])([CH3:41])([CH3:39])[CH3:40]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86699816(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-1H-pyrazolo[4,3-b]pyridine-6-yl)benzo[d]thiazol-6-yl)ethyl pivalate

Product 1

HCID 86699817(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-1H-pyrazolo[4,3-b]pyridin-6-yl)benzo[d]thiazol-6-yl)ethanol

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-1H-pyrazolo[4,3-b]pyridine-6-yl)benzo[d]thiazol-6-yl)ethyl pivalate: (68 mg, 0.115 mmol) in THF/CH3OH (1.5 mL/1.5 mL) was added 2N NaOH (0.57 mL, 1.15 mmol). The reaction mixture was heated at 45° C. for 2 h and cooled to rt. The reaction solution is quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The organic solution is washed with water, brine, dried and concentrated to give crude product which was carried to next reaction without further purification. LCMS-ESI+: calc'd for C27H27ClN4O2S: 507.16 (M+H+); Found: 507.2 (M+H+).

Workup

  1. temperaturecooled to rt
  2. customThe reaction solution is quenched with saturated ammonium chloride solution
  3. extractionextracted with ethyl acetate
  4. washThe organic solution is washed with water, brine
  5. customdried
  6. concentrationconcentrated
  7. customto give crude product which
  8. customwas carried to next reaction without further purification

Sources & evidence

ORD record
ord-b5e4a9450ae341e8aabf65344ab64804
Source dataset
uspto-grants-2015_08
Patent number
US09096586B2

Reaction notes

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