Acetic Acid → N-benzyl-N-nitroso-2-cyclohexyl-2-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-acetamide

HRID 417112노트

반응식

HRID 417112 반응식
[CH2:1]([NH:8][C:9](=[O:38])[CH:10]([CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)[N:11]1[C:15]2[CH:16]=[C:17]([F:21])[C:18]([F:20])=[CH:19][C:14]=2[N:13]=[C:12]1[C:22]1[C:23]([O:30][CH3:31])=[N:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.C(OC(=O)C)(=O)C.[N:50]([O-])=[O:51].[Na+]>>[CH2:1]([N:8]([N:50]=[O:51])[C:9](=[O:38])[CH:10]([CH:32]1[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1)[N:11]1[C:15]2[CH:16]=[C:17]([F:21])[C:18]([F:20])=[CH:19][C:14]=2[N:13]=[C:12]1[C:22]1[C:23]([O:30][CH3:31])=[N:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 4

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 23668193Sodium NitriteHCID 66619365N-Benzyl-2-cyclohexyl-2-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-acetamide

생성물 1

HCID 86639899N-benzyl-N-nitroso-2-cyclohexyl-2-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-acetamide

실험 절차

To an ice-cold solution of 15 g (28.81 mmol) N-benzyl-2-cyclohexyl-2-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-acetamide in 94 ml (1642 mmol) acetic acid and 198 ml (3486 mmol) acetic anhydride were added in 5 portions over 30 min. 9.94 g (144 mmol) sodium nitrite. The resulting solution was allowed to warm to room temperature overnight. The resulting yellow suspension was evaporated and the yellow slurry was taken up in 500 ml saturated aqueous sodium bicarbonate solution and 1500 ml ethyl acetate. The aqueous layer was extracted twice with 1500 ml ethyl acetate and once with 500 ml ethyl acetate. The combined organic layers were washed with water and brine. The remaining unsoluble material was filtered off and the filtrate dried over magnesium sulfate, filtered and evaporated until a suspension has formed. This suspensions was filtered and the filter cake washed twice with 50 ml ice-cold ethyl acetate and dried in high vacuum. Light yellow solid. MS (Turbo Spray): m/z=550.3 [M+H].

후처리

  1. customThe resulting yellow suspension was evaporated
  2. extractionThe aqueous layer was extracted twice with 1500 ml ethyl acetate and once with 500 ml ethyl acetate
  3. washThe combined organic layers were washed with water and brine
  4. filtrationThe remaining unsoluble material was filtered off
  5. dry with materialthe filtrate dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated until a suspension
  8. customhas formed
  9. filtrationThis suspensions was filtered
  10. washthe filter cake washed twice with 50 ml ice-cold ethyl acetate
  11. customdried in high vacuum

출처 및 근거

ORD 기록
ord-9980bcf8fabc4567bdc41d2383a8de8f
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088930B2

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