Sodium Bicarbonate → [10-(4-Chlorophenyl)-8-(2,2-difluoroethyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone

HRID 73016

反応式

HRID 73016 の反応式
FC(F)(F)S(O[CH2:7][CH:8]([F:10])[F:9])(=O)=O.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[O:43][C:24]3([CH2:29][CH2:28][N:27]([C:30]([C:32]4[CH:37]=[CH:36][C:35]([O:38][CH:39]([CH3:41])[CH3:40])=[C:34]([CH3:42])[CH:33]=4)=[O:31])[CH2:26][CH2:25]3)[CH2:23][NH:22][CH2:21]2)=[CH:16][CH:15]=1.C([O-])(O)=O.[Na+]>C(O)C>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[O:43][C:24]3([CH2:25][CH2:26][N:27]([C:30]([C:32]4[CH:37]=[CH:36][C:35]([O:38][CH:39]([CH3:40])[CH3:41])=[C:34]([CH3:42])[CH:33]=4)=[O:31])[CH2:28][CH2:29]3)[CH2:23][N:22]([CH2:7][CH:8]([F:10])[F:9])[CH2:21]2)=[CH:16][CH:15]=1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 27740892,2-Difluoroethyl trifluoromethanesulfonateHCID 70872702[10-(4-Chlorophenyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone

生成物 1

HCID 86672477[10-(4-Chlorophenyl)-8-(2,2-difluoroethyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone収率 106.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

2,2-difluoroethyl trifluoromethanesulfonate (17 mg, 0.08 mmol) was added to a solution of [10-(4-chlorophenyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone (22 mg, 0.05 mmol) and NaHCO3 (13 mg, 0.15 mmol) in anhydrous ethanol (0.3 mL) at room temperature. The reaction mixture was purged with argon, sealed with a cap and heated at 70° C. for 40 minutes. The reaction mixture was cooled to room temperature, diluted with MeOH to 1 mL, microfiltered and purified by Waters mass directed LC/MS: (10-99% ACN/H2O (5 mM HCl)) to yield [10-(4-chlorophenyl)-8-(2,2-difluoroethyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone (27 mg, 100%). ESI-MS m/z calc. 506.21478. Found 507.2 (M+1)+; Retention time: 2.17 minutes (3 min run).

後処理

  1. customThe reaction mixture was purged with argon
  2. customsealed with
  3. customa cap
  4. temperatureThe reaction mixture was cooled to room temperature
  5. additiondiluted with MeOH to 1 mL
  6. custommicrofiltered and purified by Waters mass

出典と根拠

ORDレコード
ord-13e8da07d543418abb593c868fbb31a8
出典データセット
uspto-grants-2014_09
特許番号
US08828996B2

関連ノート

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