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Triethylamine → Ethyl (2S)-2-(tert-butoxy)-2-[4,23-dimethyl-22-oxa-1,5,7,8-tetraazapentacyclo[21.2.2.16,9.02,7.013,18]octacosa-2,4,6(28),8,10,13(18),14,16,19-nonaen-3-yl]acetate

HRID 921104
ノート
印刷プレビュー

反応式

HRID 921104 の反応式
[CH2:1]([O:4][C:5]1([CH3:42])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[N:17]=[C:18]([CH:20]=[CH:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4Br)[CH:19]=[C:15]3[N:14]=[C:13]([CH3:30])[C:12]=2[C@H:31]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:7][CH2:6]1)[CH:2]=[CH2:3].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(#N)C>[C:38]([O:37][C@@H:31]([C:12]1[C:13]([CH3:30])=[N:14][C:15]2=[CH:19][C:18]3=[N:17][N:16]2[C:11]=1[N:8]1[CH2:9][CH2:10][C:5]([CH3:42])([O:4][CH2:1][CH:2]=[CH:3][C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:22][CH:21]=[CH:20]3)[CH2:6][CH2:7]1)[C:32]([O:34][CH2:35][CH3:36])=[O:33])([CH3:40])([CH3:41])[CH3:39]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 123595847(S)-Ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-(2-bromophenyl)prop-1-en-1-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

生成物 1

HCID 123747350Ethyl (2S)-2-(tert-butoxy)-2-[4,23-dimethyl-22-oxa-1,5,7,8-tetraazapentacyclo[21.2.2.16,9.02,7.013,18]octacosa-2,4,6(28),8,10,13(18),14,16,19-nonaen-3-yl]acetate収率 51.8%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 6342Acetonitrile溶媒

反応条件

温度
120 °C

実験手順

To a pressure tube flushed with N2 were added (S)-ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-(2-bromophenyl)prop-1-en-1-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (0.09 g, 0.141 mmol), acetonitrile (4 ml) and triethylamine (0.196 ml, 1.407 mmol). Added to this solution were triphenylphosphine (0.011 g, 0.042 mmol) and tris(dibenzylideneacetone)dipalladium (0) (0.013 g, 0.014 mmol). The tube was sealed and stirred at 120° C. After stirring for 20 h, the mixture was cooled, filtered and concentrated to give a yellow residue. The residue was purified by flash chromatography (Biotage; 0%-100% EtOAc/hexane; 20 CV) to give the title compound (0.0406 g, 0.073 mmol, 51.6% yield) as a sticky yellow oil. LCMS (M+H) calcd for C33H43N4O4: 559.32. found: 559.5.

後処理

  1. customTo a pressure tube flushed with N2
  2. additionAdded to this solution
  3. customThe tube was sealed
  4. stirringAfter stirring for 20 h
  5. temperaturethe mixture was cooled
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a yellow residue
  9. customThe residue was purified by flash chromatography (Biotage; 0%-100% EtOAc/hexane; 20 CV)

出典と根拠

ORDレコード
ord-eda557132f6640199dcc38ed95c73f14
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09273067B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート