Hydrochloric Acid → N-({6-[(2-Hydroxyethyl)amino]-4-(methylthio)pyridin-2-yl}carbamoyl)-5-(2-methoxyethyl)-4-methylthiophene-2-sulfonamide

HRID 1696750Notes

Reaction equation

HRID 1696750 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][NH:9][C:10]1[N:15]=[C:14]([NH:16][C:17]([NH:19][S:20]([C:23]2[S:24][C:25]([CH2:29][CH2:30][O:31][CH3:32])=[C:26]([CH3:28])[CH:27]=2)(=[O:22])=[O:21])=[O:18])[CH:13]=[C:12]([S:33][CH3:34])[CH:11]=1)(C)(C)C.Cl>CO>[OH:6][CH2:7][CH2:8][NH:9][C:10]1[N:15]=[C:14]([NH:16][C:17]([NH:19][S:20]([C:23]2[S:24][C:25]([CH2:29][CH2:30][O:31][CH3:32])=[C:26]([CH3:28])[CH:27]=2)(=[O:22])=[O:21])=[O:18])[CH:13]=[C:12]([S:33][CH3:34])[CH:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67273738HCID 67273738, compound

Product 1

HCID 42629875N-({6-[(2-Hydroxyethyl)amino]-4-(methylthio)pyridin-2-yl}carbamoyl)-5-(2-methoxyethyl)-4-methylthiophene-2-sulfonamideYield 63.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The below prepared N-({6-[(2-(tert-butyl-dimethyl-silanyloxy)-ethyl)amino]-4-(methylthio)pyridin-2-yl}carbamoyl)-5-(2-methoxyethyl)-4-methylthiophene-2-sulfonamide (0.160 g, 0.278 mmol) was dissolved in 5 mL of MeOH and treated with aq. HCl (1.0 mL 1 N). After 2 h at ambient temperature, the reaction mixture was poured onto icewater, twofold extracted with AcOEt, washed with water and brine, dried over magnesium sulfate, and evaporated to dryness. Crystallization from AcOEt gave 0.081 g of the title compound as off-white crystals.

Workup

  1. additionthe reaction mixture was poured onto icewater
  2. extractiontwofold extracted with AcOEt
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness
  6. customCrystallization from AcOEt

Sources & evidence

ORD record
ord-b0fe534236334865b34784227f8c8609
Source dataset
uspto-grants-2012_04
Patent number
US08163778B2

Reaction notes

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