Sodium Hydroxide → HCID 23582801, compound

HRID 2242861Notes

Reaction equation

HRID 2242861 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][N:8]([CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[C:27]([Cl:28])=[C:26]3[C:21]([CH:22]=[CH:23][CH:24]=[CH:25]3)=[N:20]2)=[CH:15][CH:14]=1)[CH3:9])C.[OH-].[Na+]>CCO.O>[Cl:28][C:27]1[N:19]([C:16]2[CH:15]=[CH:14][C:13]([O:12][CH2:11][CH2:10][N:8]([CH3:9])[CH2:7][CH2:6][CH2:5][C:4]([OH:29])=[O:3])=[CH:18][CH:17]=2)[N:20]=[C:21]2[C:26]=1[CH:25]=[CH:24][CH:23]=[CH:22]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68705319HCID 68705319, compound

Product 1

HCID 23582801HCID 23582801, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A solution of this ester from step 1 (0.1 g, 0.23 mmol) and NaOH (20 mg, 0.47 mmol) in EtOH/water (1.1, 5 mL) was stirred at room temperature for 16 h. After the ethanol was removed, the aqueous solution was acidified with 10% HCl to pH=2, extracted with ethyl acetate. The combined organic phases were dried over Na2SO4 and concentrated. The crude material was triturated with ether to yield the title compound (48 mg, 50%); 1H NMR (400 MHz, DMSO) δ 9.01 (s, 1H), 8.01 (d, J=9.2 Hz, 2H), 7.76 (d, J=8 Hz, 1H), 7.68 (d, J=8 Hz, 1H), 7.30 (m, 1H), 7.15 (d, J=8 Hz, 2H), 7.08 (m, 1H), 4.15 (t, J=12, 6 Hz, 2H), 3.27 (m, 4H), 2.84 (m, 2H), 2.76 (s, 3H), 2.18 (m, 2H); LC/MS (ESI+) m/z: 98%.

Workup

  1. customAfter the ethanol was removed
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude material was triturated with ether

Sources & evidence

ORD record
ord-31bdea1e54744b1598859a0980af3ddd
Source dataset
uspto-grants-2010_03
Patent number
US07674802B2

Reaction notes

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