Ammonium Chloride → N-Methoxy-N-methylthieno[3,2-c]pyridine-2-carboxamide

HRID 1775415Notes

Reaction equation

HRID 1775415 reaction equation
Cl.[CH3:2][O:3][NH:4][CH3:5].C([Li])CCC.CO[C:13]([C:15]1[S:23][C:22]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[CH:16]=1)=[O:14].[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[CH3:2][O:3][N:4]([CH3:5])[C:13]([C:15]1[S:23][C:22]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[CH:16]=1)=[O:14]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 22047666Methyl thieno[3,2-c]pyridine-2-carboxylateHCID 178418339Butyllithium

Product 1

HCID 86671431N-Methoxy-N-methylthieno[3,2-c]pyridine-2-carboxamideYield 51%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

A suspension of O,N-dimethylhydroxylamine hydrochloride (2.32 g, 23.8 mmol) in THF (20 mL) was purged with N2 and cooled to −78° C. before adding n-butyllithium (1.6 M in hexanes, 30.0 mL, 48.1 mmol). Removed bath and stirred 15 minutes before replacing the bath and adding a solution of thieno[3,2-c]pyridine-2-carboxylic acid methyl ester (0.92 g, 4.76 mmol) in THF (10 mL). After 45 minutes, saturated NH4Cl was added. The mixture was diluted with EtOAc; washed with water, 1 M HCl, water, 5% NaHCO3, water, and brine; dried over Na2SO4, and evaporated to give 0.54 g (51%) of an oil which solidified upon standing. The product thus obtained was used in the next step without further purification. MS m/z 223 (M+H)+.

Workup

  1. customwas purged with N2
  2. customRemoved bath
  3. waitAfter 45 minutes
  4. washwashed with water, 1 M HCl, water, 5% NaHCO3, water, and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-d842b5f6d00e40ee8a2462f6b4052748
Source dataset
uspto-grants-2016_02
Patent number
US09260450B2

Reaction notes

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