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

반응식

HRID 73016 반응식
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

참가 물질

5

반응물 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

생성물 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)methanone수율 106.5%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-13e8da07d543418abb593c868fbb31a8
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828996B2

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