Triethylamine → HCID 2673079, compound

HRID 1771504Notes

Reaction equation

HRID 1771504 reaction equation
[CH3:1][C:2]1[S:6][C:5]([NH2:7])=[N:4][CH:3]=1.[CH3:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1.C(N(CC)CC)C>O1CCOCC1>[CH3:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([NH:7][C:5]2[S:6][C:2]([CH3:1])=[CH:3][N:4]=2)=[O:14])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 3517702-Amino-5-methylthiazole

Product 1

HCID 2673079HCID 2673079, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-Methyl-thiazol-2-ylamine (22.8 mg, 0.200 mmol) and 4-methyl-benzoyl chloride (30.9 mg, 0.200 mmol) were dissolved in 1,4-dioxane (2 mL) containing triethylamine (84.1 μL, 0.600 mmol). The reaction mixture was stirred overnight at room temperature. The crude product was filtered, evaporated to dryness, dissolved in 1 mL of dimethylsulfoxide and purified by reverse-phase preparative liquid chromatography (9.29 mg, 0.400, 20.0%). ESI-MS m/z calc. 232.1, found 233.2 (M+1)+ Retention time 2.65 minutes.

Workup

  1. filtrationThe crude product was filtered
  2. customevaporated to dryness
  3. dissolutiondissolved in 1 mL of dimethylsulfoxide
  4. custompurified by reverse-phase preparative liquid chromatography (9.29 mg, 0.400, 20.0%)

Sources & evidence

ORD record
ord-8ac1d5f51a4e4a5d90ab9afeadad1b83
Source dataset
uspto-grants-2016_02
Patent number
US09249131B2

Reaction notes

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