Diisopropylethylamine → (3Z)-1-ethyl-1-methyl-3-[5-methyl-3-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-ylidene]urea

HRID 390719노트

반응식

HRID 390719 반응식
[I-].C[N+]1[CH:7]=[CH:6][N:5]([C:8](/[N:10]=[C:11]2\[S:12][C:13]([CH3:26])=[CH:14][N:15]\2[C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)=[O:9])[CH:4]=1.C(N(C(C)C)CC)(C)C.Cl.CNCC>C(#N)C>[CH2:6]([N:5]([CH3:4])[C:8](/[N:10]=[C:11]1\[S:12][C:13]([CH3:26])=[CH:14][N:15]\1[C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:24])([F:25])[F:23])=[CH:18][CH:17]=1)=[O:9])[CH3:7]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 522048Ethanamine, N-methyl-, hydrochloride (1:1)HCID 87447393(NZ)-3-methyl-N-[5-methyl-3-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-ylidene]imidazol-3-ium-1-carboxamide;iodide

생성물 1

HCID 42645131(3Z)-1-ethyl-1-methyl-3-[5-methyl-3-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-ylidene]urea

시약·촉매·용매 1

HCID 6342Acetonitrile용매3회

실험 절차

In a 20 mL vial, a solution of 3-methyl-1-({[(2Z)-5-methyl-3-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2(3H)-ylidene]amino}carbonyl)-1H-imidazol-3-ium iodide (50 mg, 0.10 mmol, Example 18B) dissolved in acetonitrile (0.6 mL) was added followed by the addition of diisopropylethylamine (28 μL, 0.13 mmol) dissolved in acetonitrile (0.6 mL). Then, to the solution was added N-methylethanamine hydrochloride (11 mg, 0.11 mmol) dissolved in acetonitrile (0.5 mL). The vial was capped and shaken overnight at room temperature. The reaction was concentrated to dryness. The residue was purified by reverse phase HPLC (C18, gradient 10-95% acetonitrile/water/0.1% trifluoroacetic acid) to provide the title compound.

후처리

  1. additionwas added
  2. customThe vial was capped
  3. concentrationThe reaction was concentrated to dryness
  4. customThe residue was purified by reverse phase HPLC (C18, gradient 10-95% acetonitrile/water/0.1% trifluoroacetic acid)

출처 및 근거

ORD 기록
ord-8cf81706133640c7953eb0bca23b9ba2
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383657B2

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