N,N-Dimethylglycine → HCID 67081163、化合物

HRID 510773ノート

反応式

HRID 510773 の反応式
Br[C:2]1[CH:19]=[CH:18][C:5]([C:6]([NH:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[O:7])=[CH:4][C:3]=1[CH3:20].[Cl:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][C:31]=1[OH:32])[O:28][CH2:27][CH2:26][CH:25]2[C:33]([O:35][CH2:36][CH3:37])=[O:34].CN(C)CC(O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.[Cu]Cl>[Cl:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][C:31]=1[O:32][C:2]1[CH:19]=[CH:18][C:5]([C:6](=[O:7])[NH:8][CH2:9][CH2:10][C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[CH:4][C:3]=1[CH3:20])[O:28][CH2:27][CH2:26][CH:25]2[C:33]([O:35][CH2:36][CH3:37])=[O:34]

参加物

7

反応物 4

HCID 673N,N-DimethylglycineHCID 10796Cesium carbonateHCID 53393319Ethyl-6-chloro-7-hydroxy-3,4-dihydro-2H-chromene-4-carboxylateHCID 670809004-Bromo-N-[2-(4-chlorophenyl)ethyl]-3-methylbenzamide

生成物 1

HCID 67081163HCID 67081163、化合物収率 21.4%

試薬・触媒・溶媒 2

HCID 62652Cuprous chloride触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a solution of 4-bromo-N-(4-chlorophenethyl)-3-methylbenzamide (0.0831 g, 0.236 mmol), ethyl 6-chloro-7-hydroxychroman-4-carboxylate (0.050 g, 0.195 mmol), and 2-(dimethylamino)acetic acid (0.0104 g, 0.101 mmol) in dioxane (1 ml) degassed with argon was added cesium carbonate (0.133 g, 0.409 mmol) and copper(I) chloride (0.0100 g, 0.101 mmol). The reaction was sealed in a screw-cap vial and heated to 100° C. for 16 hours. The reaction was cooled to ambient temperature, then loaded directly onto a Biotage SP1 system, eluting with a linear gradient of 5-70% EtOAc in hexanes to yield 22 mg of the title compound (21% yield).

後処理

  1. customThe reaction was sealed in a screw-cap vial and
  2. temperatureThe reaction was cooled to ambient temperature
  3. washeluting with a linear gradient of 5-70% EtOAc in hexanes

出典と根拠

ORDレコード
ord-fe0c41ae3aaf4aa6b01c8d6ee6cfb7bc
出典データセット
uspto-grants-2015_08
特許番号
US09096567B2

反応ノート

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