Oxalyl chloride → 4-(5-{6-[2-(Methoxymethyl)pyrrolidin-1-yl]-5-methylpyridin-3-yl}-1,2,4-oxadiazol-3-yl)benzenesulfonamide

HRID 219922

반응식

HRID 219922 반응식
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][CH2:9][CH:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15]1[C:23]([CH3:24])=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=1.[NH2:25][S:26]([C:29]1[CH:34]=[CH:33][C:32]([C:35](=[N:37]O)[NH2:36])=[CH:31][CH:30]=1)(=[O:28])=[O:27].C(C1C=CC(S(N)(=O)=O)=CC=1)#N.CCN(C(C)C)C(C)C>>[CH3:7][O:8][CH2:9][CH:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15]1[N:16]=[CH:17][C:18]([C:19]2[O:21][N:37]=[C:35]([C:32]3[CH:31]=[CH:30][C:29]([S:26]([NH2:25])(=[O:27])=[O:28])=[CH:34][CH:33]=3)[N:36]=2)=[CH:22][C:23]=1[CH3:24]

참가 물질

6

반응물 5

HCID 65578Oxalyl chlorideHCID 76566p-CyanobenzenesulphonamideHCID 81531DiisopropylethylamineHCID 612025N-hydroxy-4-sulfamoylbenzene-1-carboximidamideHCID 594958236-[2-(Methoxymethyl)pyrrolidin-1-yl]-5-methylnicotinic acid

생성물 1

HCID 252564724-(5-{6-[2-(Methoxymethyl)pyrrolidin-1-yl]-5-methylpyridin-3-yl}-1,2,4-oxadiazol-3-yl)benzenesulfonamide

실험 절차

Oxalyl chloride (122 mL; 1.44 mmol), Intermediate 29 (120 mg; 0.48 mmol), 4-(aminosulfonyl)-N′-hydroxybenzenecarboximidamide, prepared as described in WO 2006/013104 A1 from 4-cyanobenzene-1-sulfonamide (ABCR; CD10716), (103 mg; 0.48 mmol, 1 eq.) and DIEA (248 mL; 1.44 mmol) were reacted according to the procedure described for Example 38. Purification by column chromatography (from cHex/EtOAc, 50/50 to EtOAc) followed by recrystallisation from DCM/n-pentane afforded the title compound as a yellow solid. LC/MS (Method A): 430.3 (M+H)+. HPLC (Method A) Rt 2.80 min (purity 93.1%).

후처리

  1. customwere reacted
  2. customPurification by column chromatography (from cHex/EtOAc, 50/50 to EtOAc)
  3. customfollowed by recrystallisation from DCM/n-pentane

출처 및 근거

ORD 기록
ord-9f2657bfda694a018f714d5bbfa4d27f
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202865B2

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