Triethylamine → 2-(4-Fluoro-phenyl)-7,10-bis-methanesulfonyl-5-methylene-5,6,7,8,9,10-hexahydro-1-oxa-7,10,11-triaza-cycloocta[f]indene-3-carboxylic acid methylamide

HRID 2190185ノート

反応式

HRID 2190185 の反応式
[CH3:1][NH:2][C:3]([C:5]1[C:13]2[CH:12]=[C:11]3[C:14](=[CH2:24])[CH2:15][NH:16][CH2:17][CH2:18][N:19]([S:20]([CH3:23])(=[O:22])=[O:21])[C:10]3=[N:9][C:8]=2[O:7][C:6]=1[C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)=[O:4].[CH3:32][S:33](Cl)(=[O:35])=[O:34].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][NH:2][C:3]([C:5]1[C:13]2[CH:12]=[C:11]3[C:14](=[CH2:24])[CH2:15][N:16]([S:33]([CH3:32])(=[O:35])=[O:34])[CH2:17][CH2:18][N:19]([S:20]([CH3:23])(=[O:22])=[O:21])[C:10]3=[N:9][C:8]=2[O:7][C:6]=1[C:25]1[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=1)=[O:4]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 666644732-(4-Fluoro-phenyl)-10-methanesulfonyl-5-methylene-5,6,7,8,9,10-hexahydro-1-oxa-7,10,11-triaza-cycloocta[f]indene-3-carboxylic acid methylamide

生成物 1

HCID 666642522-(4-Fluoro-phenyl)-7,10-bis-methanesulfonyl-5-methylene-5,6,7,8,9,10-hexahydro-1-oxa-7,10,11-triaza-cycloocta[f]indene-3-carboxylic acid methylamide収率 44.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

2-(4-Fluoro-phenyl)-10-methanesulfonyl-5-methylene-5,6,7,8,9,10-hexahydro-1-oxa-7,10,11-triaza-cycloocta[f]indene-3-carboxylic acid methylamide (6.0 mg, 0.013 mmol) is dissolved in DCM (2 mL) and the solution is cooled to 0° C. Methanesulfonyl chloride (7.7 mg, 0.07 mmol) is added followed by triethylamine (6.83 mg, 0.07 mmol) and the reaction is allowed to warm up to RT over 3 h then evaporated to dryness and placed on the high vacuum overnight. The sample is then redissolved in EtOAc (25 mL) and then washed with 1N HCl (10 mL), then Brine (20 mL) and dried over Na2SO4. The organic is concentrated to afford 2-(4-Fluoro-phenyl)-7,10-bis-methanesulfonyl-5-methylene-5,6,7,8,9,10-hexahydro-1-oxa-7,10,11-triaza-cycloocta[f]indene-3-carboxylic acid methylamide (3 mg, 42%). MS-ES [M+H]+=523.0.

後処理

  1. temperatureto warm up to RT over 3 h
  2. customthen evaporated to dryness
  3. customplaced on the high vacuum overnight
  4. dissolutionThe sample is then redissolved in EtOAc (25 mL)
  5. washwashed with 1N HCl (10 mL)
  6. dry with materialBrine (20 mL) and dried over Na2SO4
  7. concentrationThe organic is concentrated

出典と根拠

ORDレコード
ord-825c9085c554484d81cb3c266e732492
出典データセット
uspto-grants-2012_12
特許番号
US08324239B2

反応ノート

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