Hydrochloric Acid → HCID 178520554, compound

HRID 1480444Notes

Reaction equation

HRID 1480444 reaction equation
C(OC[N:9]1[CH:13]=[C:12]([CH2:14][CH2:15][CH2:16][C:17]([NH:19][CH:20]2[CH2:25][CH2:24][N:23]([C:26](=[O:37])/[CH:27]=[CH:28]/[C:29]3[CH:34]=[C:33]([Cl:35])[CH:32]=[C:31]([Cl:36])[CH:30]=3)[CH2:22][CH2:21]2)=[O:18])[N:11]=[N:10]1)(=O)C(C)(C)C.[OH-].[Na+].Cl>CO>[Cl:35][C:33]1[CH:34]=[C:29](/[CH:28]=[CH:27]/[C:26]([N:23]2[CH2:22][CH2:21][CH:20]([NH:19][C:17](=[O:18])[CH2:16][CH2:15][CH2:14][C:12]3[N:11]=[N:10][NH:9][CH:13]=3)[CH2:25][CH2:24]2)=[O:37])[CH:30]=[C:31]([Cl:36])[CH:32]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86722670(E)-(4-(4-((1-(3-(3,5-Dichlorophenyl)acryloyl)piperidin-4-yl)amino)-4-oxobutyl)-1H-1,2,3-triazol-1-yl)methyl pivalate

Product 1

HCID 178520554HCID 178520554, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (E)-(4-(4-((1-(3-(3,5-dichlorophenyl)acryloyl)piperidin-4-yl)amino)-4-oxobutyl)-1H-1,2,3-triazol-1-yl)methyl pivalate (284 mg, 0.516 mmol) in MeOH (1 mL) was added 1M NaOH (1.135 mL, 1.135 mmol) and the mixture allowed to stir at RT for 1.5 hrs. An equivalent of 1M HCl (1.1 ml) was added to neutralise the reaction mixture and the MeOH was removed under reduced pressure. The reaction mixture was diluted with EtOAc and washed with water. The organic portion was dried over MgSO4, filtered and concentrated under reduced pressure. Purification was carried out by chromatography on silica using 0-10% MeOH in DCM to afford the title product;

Workup

  1. customthe MeOH was removed under reduced pressure
  2. additionThe reaction mixture was diluted with EtOAc
  3. washwashed with water
  4. dry with materialThe organic portion was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification

Sources & evidence

ORD record
ord-01be150c2c224f4b9c5cd6b15d8b2140
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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