Sodium Hydroxide → HCID 86699831, compound

HRID 510298Notes

Reaction equation

HRID 510298 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[CH:25]=[N:24][N:23]([CH3:26])[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[CH:25]=[N:24][N:23]([CH3:26])[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)[CH2:8][OH:7])([CH3:41])([CH3:39])[CH3:40]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86699832HCID 86699832, compound

Product 1

HCID 86699831HCID 86699831, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of compound (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)benzo[d]thiazol-6-yl)ethyl pivalate (14 mg, 0.024 mmol) in THF (0.50 mL) and MeOH (0.50 mL) was added aqueous NaOH (0.10 mL of a 2 N solution). The reaction mixture was heated at 50° C. for 17 h, cooled, diluted with satd. aqueous NH4Cl and extracted with ethyl acetate. The organic layer was dried and concentrated to give the desired product which was used without any further purification. LCMS-ESI+: calc'd for C27H28ClN4O2S: 507.2 (M+H+); 507.2 (M+H+).

Workup

  1. temperaturecooled
  2. additiondiluted with satd
  3. extractionaqueous NH4Cl and extracted with ethyl acetate
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-aeaa73939ca94cf0aecae043a2921856
Source dataset
uspto-grants-2015_08
Patent number
US09096586B2

Reaction notes

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