Diethylene Glycol Monomethyl Ether → N-(2-{[3-Chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)-succinamic acid 2-(2-methoxy-ethoxy)ethyl ester

HRID 1797316

반응식

HRID 1797316 반응식
CCOC(/N=N/C(OCC)=O)=O.[Cl:13][C:14]1[CH:15]=[C:16]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[NH:36][C:37](=[O:43])[CH2:38][CH2:39][C:40]([OH:42])=[O:41])[CH:17]=[CH:18][C:19]=1[C:20](=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:63][O:64][CH2:65][CH2:66][O:67][CH2:68][CH2:69]O>C1(C)C=CC=CC=1.CCOC(C)=O.O>[CH3:63][O:64][CH2:65][CH2:66][O:67][CH2:68][CH2:69][O:41][C:40](=[O:42])[CH2:39][CH2:38][C:37]([NH:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[NH:29][C:16]1[CH:17]=[CH:18][C:19]([C:20](=[O:28])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])=[C:14]([Cl:13])[CH:15]=1)=[O:43]

참가 물질

8

반응물 4

HCID 8134Diethylene Glycol Monomethyl EtherHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 9845903N-[2-[3-Chloro-4-(2-methylbenzoyl)-phenylamino]phenyl]-succinamic Acid

생성물 1

HCID 69663252N-(2-{[3-Chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)-succinamic acid 2-(2-methoxy-ethoxy)ethyl ester

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of diethylazodicarboxylate (40% in toluene, 229 μL, 0.5 mmol) was slowly added to a mixture of N-(2-{[3-chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)-succinamic acid (200 mg, 0.46 mmol) (disclosed in WO 01/05746), triphenylphosphine (132 mg, 0.50 mmol), and 2-(2-methoxyethoxy)ethanol (55 mg, 0.46 mmol) in dry toluene (2.5 ml). The reaction mixture was stirred for 48 h and then poured into a mixture of water and EtOAc. The aqueous phase was extracted with more EtOAc (×2). The combined organic phases were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using EtOAc as the eluent to afford the title compound as a yellow oil.

후처리

  1. extractionThe aqueous phase was extracted with more EtOAc (×2)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-3b3b7a0bd78c440686b1c6c5346051a3
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07034015B2

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