Sodium Carbonate → N-Cyclopropyl-3-(3-{2-[(2-hydroxyethyl)amino]-2-oxoethyl}-1,2-benzisoxazol-6-yl)-4-methylbenzamide

HRID 1988926노트

반응식

HRID 1988926 반응식
[CH:1]1([CH2:4][NH:5][C:6](=[O:22])[C:7]2[CH:12]=[CH:11][CH:10]=[C:9](B3OC(C)(C)C(C)(C)O3)[CH:8]=2)[CH2:3]C1.Br[C:24]1[CH:39]=[CH:38][C:27]2[C:28]([CH2:31][C:32]([NH:34][CH2:35][CH2:36][OH:37])=[O:33])=[N:29][O:30][C:26]=2[CH:25]=1.[C:40](=O)([O-])[O-].[Na+].[Na+]>C(O)(C)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:4]1([NH:5][C:6](=[O:22])[C:7]2[CH:12]=[CH:11][C:10]([CH3:40])=[C:9]([C:24]3[CH:39]=[CH:38][C:27]4[C:28]([CH2:31][C:32]([NH:34][CH2:35][CH2:36][OH:37])=[O:33])=[N:29][O:30][C:26]=4[CH:25]=3)[CH:8]=2)[CH2:1][CH2:3]1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 586564962-(6-bromo-1,2-benzisoxazol-3-yl)-N-(2-hydroxyethyl)acetamide2회HCID 68676775HCID 68676775, 화합물2회

생성물 1

HCID 10453183N-Cyclopropyl-3-(3-{2-[(2-hydroxyethyl)amino]-2-oxoethyl}-1,2-benzisoxazol-6-yl)-4-methylbenzamide

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 3776Isopropanol용매

실험 절차

A mixture of N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Intermediate 5) (0.04 g) 2-(6-bromo-1,2-benzisoxazol-3-yl)-N-(2-hydroxyethyl)acetamide (Intermediate 35) (0.04 g) 2M aqueous sodium carbonate (1.5 ml) and tetrakis(triphenylphosphine)palladium(0) (1 mg) in isopropanol (3 ml) was stirred at reflux under nitrogen for 18 h. The mixture was absorbed onto silica (Merck 7734) and applied to a Varian Bond-Elut SPE cartridge (silica, 5 g) and eluted with a toluene:ethanol gradient (100:0 to 0:100) to give the title compound as a white solid (0.03 g).

후처리

  1. temperatureat reflux under nitrogen for 18 h
  2. customThe mixture was absorbed onto silica (Merck 7734)
  3. washeluted with a toluene

출처 및 근거

ORD 기록
ord-f8dd1ace81eb419484916977c6880292
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07642276B2

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