Ethyl 3-bromopropionate → Ethyl 3-[9-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]propanoate

HRID 1514247ノート

反応式

HRID 1514247 の反応式
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[C:28]4[O:27][CH2:26][CH2:25][NH:24][CH2:23][C:22]=4[CH:21]=[CH:20][CH:19]=3)[N:14]=2)[CH:6]=[N:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11].C(N(CC)C(C)C)(C)C.Br[CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42]>C(#N)C>[Cl:2][C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[C:28]4[O:27][CH2:26][CH2:25][N:24]([CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:23][C:22]=4[CH:21]=[CH:20][CH:19]=3)[N:14]=2)[CH:6]=[N:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11]

参加物

5

反応物 3

HCID 68320Ethyl 3-bromopropionate2 回HCID 81531Diisopropylethylamine2 回HCID 684690769-(5-{5-Chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine hydrochloride

生成物 1

HCID 59403487Ethyl 3-[9-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]propanoate収率 30.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

To a solution of 9-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine hydrochloride (Preparation 90) (80 mg, 0.189 mmol) in acetonitrile (10 ml) was added N,N-diisopropylethylamine (0.066 ml, 0.378 mmol) followed by ethyl 3-bromopropanoate (0.048 ml, 0.378 mmol). The reaction mixture was heated at 80° C. overnight. A further 1 equivalent of N,N-diisopropylethylamine and ethyl 3-bromopropanoate were added and heating continued overnight. The reaction mixture was cooled and evaporated. The residue was purified by column chromatography on silica. Elution with 40-60% ethyl acetate in cyclohexane to give the title compound as an olive green coloured oil (28 mg).

後処理

  1. temperatureheating continued overnight
  2. temperatureThe reaction mixture was cooled
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica
  5. washElution with 40-60% ethyl acetate in cyclohexane

出典と根拠

ORDレコード
ord-bf6b27dfdb5b4259b980e3138beeeda9
出典データセット
uspto-grants-2012_07
特許番号
US08222245B2

反応ノート

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