Sodium Hydroxide → HCID 16049114, compound

HRID 2357988Notes

Reaction equation

HRID 2357988 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:13]=2)[C:8]([NH:22][C:23]2[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:30])=[N:7]1)C.[OH-].[Na+]>CO>[CH3:30][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]([CH3:29])[C:23]=1[NH:22][C:8]1[C:9]2[C:14](=[CH:13][C:12]([NH:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:11][CH:10]=2)[N:6]([CH2:5][C:4]([OH:31])=[O:3])[N:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 16049048HCID 16049048, compound

Product 1

HCID 16049114HCID 16049114, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 300 mg (0.72 mmol) of ethyl 2-(3-(2,6-dimethylphenylamino)-6-(phenylamino)-1H-indazol-1-yl)acetate 64 (Example 29) in MeOH (10 mL) was added 1 N NaOH solution (4 mL, 4 mmol). The mixture was stirred at room temperature for 8 hours before being concentrated under reduced pressure. The residue was extracted with DCM (5 mL×2) and neutralized with 3 N HCl solution to pH 2. The resulting yellow solid was filtered, washed with water and dried to give the title compound. 1H-NMR (DMSO-d6) δ 2.20 (s, 6H), 4.74 (s, 2H), 6.96 (t, J=7.2 Hz, 1H), 7.05-7.09 (m, 3H), 7.28 (t, J=7.7 Hz, 2H), 7.79 (d, J=7.9 Hz, 2H), 8.22 (s, 1H), 8.53 (s, 1H), 9.77 (s, 1H). Mass Spectrum (ESI) m/e=389 (M+1).

Workup

  1. concentrationbefore being concentrated under reduced pressure
  2. extractionThe residue was extracted with DCM (5 mL×2)
  3. filtrationThe resulting yellow solid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-331f67a8e0c04de385f56a57b872f10c
Source dataset
uspto-grants-2010_07
Patent number
US07763624B2

Reaction notes

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