Hydrochloric Acid → 2-{[6-(Morpholin-4-ylmethyl)pyridin-2-yl]amino}-5-(1H-1,2,3-triazol-4-yl)thiophene-3-carboxamide

HRID 386143Notes

Reaction equation

HRID 386143 reaction equation
C(OC[N:9]1[CH:13]=[C:12]([C:14]2[S:15][C:16]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)[N:24]=3)=[C:17]([C:19]([NH2:21])=[O:20])[CH:18]=2)[N:11]=[N:10]1)(=O)C(C)(C)C.[OH-].[Na+].Cl>CO.O>[N:30]1([CH2:29][C:25]2[N:24]=[C:23]([NH:22][C:16]3[S:15][C:14]([C:12]4[N:11]=[N:10][NH:9][CH:13]=4)=[CH:18][C:17]=3[C:19]([NH2:21])=[O:20])[CH:28]=[CH:27][CH:26]=2)[CH2:31][CH2:32][O:33][CH2:34][CH2:35]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59525795[4-(4-(Aminocarbonyl)-5-{[6-(morpholin-4-ylmethyl)pyridin-2-yl]amino}-2-thienyl)-1H-1,2,3-triazol-1-yl]methyl pivalate

Product 1

HCID 1785135682-{[6-(Morpholin-4-ylmethyl)pyridin-2-yl]amino}-5-(1H-1,2,3-triazol-4-yl)thiophene-3-carboxamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a suspension of [4-(4-(aminocarbonyl)-5-{[6-(morpholin-4-ylmethyl)pyridin-2-yl]amino}-2-thienyl)-1H-1,2,3-triazol-1-yl]methyl pivalate (70 mg, 0.14 mmol) in MeOH (1.5 mL) and water (1.0 mL) was added NaOH (1.0 M, 0.310 ml, 0.31 mmol). The mixture was stirred at room temperature for 45 min (the suspension became a clear orange solution). The reaction was neutralized with 2 N HCl (0.150 ml), diluted with water, and extracted with 5:1 CH2Cl2:MeOH (3×). The combined organic extracts were dried (MgSO4), filtered, combined with silica gel, and evaporated to dryness. Flash chromatography (dry load, 0-10% MeOH/CH2Cl2) yielded the title compound as a colorless solid.

Workup

  1. extractionextracted with 5:1 CH2Cl2
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated to dryness
  5. dry with materialFlash chromatography (dry load, 0-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-55ff82842eea4085b29e2ebea4fcaad4
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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