Bicarbonate Ion → HCID 71766083, 화합물

HRID 403368노트

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HRID 403368 반응식
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][CH3:9])=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[O:17][CH3:18])[CH:3]=1.[CH3:19][S:20]([C:23]1[CH:24]=[C:25]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[C:26]([OH:28])=O)(=[O:22])=[O:21].F[B-](F)(F)F.BrC1C=CC=C[N+]=1CC.C(N(C(C)C)C(C)C)C.C(=O)(O)[O-]>ClCCl>[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]([CH3:9])[C:26](=[O:28])[C:25]2[CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=[C:23]([S:20]([CH3:19])(=[O:21])=[O:22])[CH:24]=2)=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[O:17][CH3:18])[CH:3]=1

참가 물질

7

반응물 5

HCID 769Bicarbonate IonHCID 81531DiisopropylethylamineHCID 27363002-Bromo-1-ethylpyridinium tetrafluoroborateHCID 215445163-Methanesulfonyl-5-(trifluoromethyl)benzoic acidHCID 86698474[6-Chloro-4-(4-fluoro-2-methoxy-phenyl)-pyridazin-3-yl]-methyl-amine

생성물 1

HCID 71766083HCID 71766083, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of [6-chloro-4-(4-fluoro-2-methoxy-phenyl)-pyridazin-3-yl]-methyl-amine (95 mg, 355 μmol) in dichloromethane (5 mL) was added 3-methanesulfonyl-5-trifluoromethyl-benzoic acid (95.2 mg, 355 mmol) and 2-bromo-1-ethylpyridinium tetrafluoroborate (117 mg, 426 μmol, CAS RN 878-23-9) and N-ethyldiisopropyl-amine (91.7 mg, 124 μL, 710 μmol). The reaction mixture was stirred at room temperature for 72 hours and then poured on 30 mL 10% aqueous bicarbonate solution and 30 mL dichloromethane and the layers were separated. The aqueous layer was extracted a second time with 30 mL dichloromethane. The organic layers were washed with 30 mL brine, dried over magnesium sulfate, filtered and concentrated under vacuum. The compound was purified by silica gel chromatography on a 20 g column using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:ethyl acetate (100:0 to 0:100). Colorless solid (63 mg, 34.3%). MS (ESI+): m/z=518.056 ([M+H]+).

후처리

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted a second time with 30 mL dichloromethane
  3. washThe organic layers were washed with 30 mL brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe compound was purified by silica gel chromatography on a 20 g column
  8. washeluting with a gradient of n-heptane:ethyl acetate (100:0 to 0:100)

출처 및 근거

ORD 기록
ord-a64216ca754e488eac254939146428b3
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748434B2

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