Hydrochloric Acid → HCID 57652738, compound

HRID 424837Notes

Reaction equation

HRID 424837 reaction equation
C([O:3][C:4](=[O:39])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N:11]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[N:23]([C:30]4[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:31]=4[Cl:37])[N:24]=[N:25][C:26]=3[CH:27]([CH3:29])[CH3:28])=[CH:16][C:15]=2[CH3:38])[CH3:12])[CH:6]=1)C.[OH-].[Na+].Cl>C1COCC1.CO>[Cl:36][C:35]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:37])[C:30]=1[N:23]1[C:22]([CH2:21][O:20][C:17]2[CH:18]=[CH:19][C:14]([CH2:13][N:11]([CH3:12])[C:7]3[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=3)[C:4]([OH:39])=[O:3])=[C:15]([CH3:38])[CH:16]=2)=[C:26]([CH:27]([CH3:29])[CH3:28])[N:25]=[N:24]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66704170HCID 66704170, compound

Product 1

HCID 57652738HCID 57652738, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-({4-[3-(2,6-Dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-benzyl}-methyl-amino)-benzoic acid ethyl ester (20 mg, 0.035 mmol) in THF (4.0 mL) and methanol (4.0 mL) is added 5 M NaOH (0.5 mL). The reaction mixture is heated to 70° C. for two hours and cooled to room temperature. A solution of 5 M HCl (0.5 mL) is added. The reaction mixture is concentrated and triturated with methanol and then water is added to precipitate the product. The title compound (10 mg, 53%) is collected by vacuum filtration as a white solid. LC-MS: 537.3 (M−1).

Workup

  1. temperaturecooled to room temperature
  2. concentrationThe reaction mixture is concentrated
  3. customtriturated with methanol
  4. additionwater is added
  5. customto precipitate the product
  6. filtrationThe title compound (10 mg, 53%) is collected by vacuum filtration as a white solid

Sources & evidence

ORD record
ord-4984dfe982f8434488948153de556b68
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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