Triethylamine → HCID 89312411, compound

HRID 2174177Notes

Reaction equation

HRID 2174177 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:8][C:9]([C:12](Cl)=[O:13])=[CH:10][N:11]=2)[CH:2]=1.C(N(CC)CC)C.Cl.[CH3:23][O:24][NH:25][CH3:26]>C(Cl)Cl.CN(C1C=CC=CN=1)C>[CH3:23][O:24][N:25]([CH3:26])[C:12]([C:9]1[S:8][C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[N:11][CH:10]=1)=[O:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 58236112HCID 58236112, compound

Product 1

HCID 89312411HCID 89312411, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of 2-(3-pyridyl)thiazole-5-carbonyl chloride (4.6 g, 19.5 mmol) prepared according to WO 2009/149858) in methylene chloride (100 ml) was cooled to 0° C. and treated with triethyl amine (6.03 g, 58.4 mmol), dimethylamino pyridine (12 mg, 0.097 mmol) and then N-methoxymethanamine hydrochloride (2.9 g, 29.2 mmol). The mixture was allowed to warm up to ambient temperature and monitored by TLC and LC/MS. After completion, the reaction mixture was diluted with methylene chloride, washed with water, dried over magnesium sulfate, and the solvent removed by concentration in vacuo, to give 3.99 g (82%) of N-methoxy-N-methyl-2-(3-pyridyl)thiazole-5-carboxamide as a pale solid.

Workup

  1. customprepared
  2. temperatureto warm up to ambient temperature
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent removed by concentration in vacuo

Sources & evidence

ORD record
ord-c057f0659ee54262b102c7d77f0ce486
Source dataset
uspto-grants-2015_06
Patent number
US09060519B2

Reaction notes

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