Diisopropylethylamine → US10385022, Example 6

HRID 877964ノート

反応式

HRID 877964 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5](Cl)=[O:6].[CH3:15][NH:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29].CCN(C(C)C)C(C)C>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([N:16]([CH3:15])[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29])=[O:6]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 5193643-Fluoro-5-(trifluoromethyl)benzoyl chlorideHCID 18403336N-methyl-4-o-tolylpyridin-3-amine

生成物 1

HCID 60197094US10385022, Example 6収率 57%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3-Fluoro-5-trifluoromethylbenzoyl chloride (92 mg, 0.41 mmol, CAS RN 171243-30-4) was added to a solution of methyl-(4-o-tolyl-pyridin-3-yl)-amine (40 mg, 0.20 mmol, example 1, intermediate a) and DIPEA (70 μL, 0.40 mmol) in THF (1 mL). After 2 h, an additional 25 μL of acyl chloride was added. The reaction mixture was stirred overnight, filtered and all volatiles removed. The resulting oil was purified by flash chromatography on silica gel eluting with 33-50% EtOAc in n-hexane to yield the product as a waxy solid (45 mg, 57%). MS (ESI): m/z=470.0 [M+H]+.

後処理

  1. filtrationfiltered
  2. customall volatiles removed
  3. customThe resulting oil was purified by flash chromatography on silica gel eluting with 33-50% EtOAc in n-hexane

出典と根拠

ORDレコード
ord-af7b6bb4788242359edbb2b600642689
出典データセット
uspto-grants-2015_03
特許番号
US08987307B2

反応ノート

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