Dimethylformamide → HCID 117675490, 화합물

HRID 1526186노트

반응식

HRID 1526186 반응식
Br[C:2]1[CH:34]=[CH:33][C:5]([O:6][C:7]2[N:12]=[C:11]([O:13][C:14]3[CH:15]=[C:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:17]=[CH:18][CH:19]=3)[C:10]([CH2:28][CH3:29])=[N:9][C:8]=2[C:30](=[O:32])[NH2:31])=[CH:4][CH:3]=1.[CH3:35][N:36]1[CH2:41][CH:40]=[C:39](B2OC(C)(C)C(C)(C)O2)[CH2:38][CH2:37]1.CN(C)C=O.C(=O)([O-])[O-].[Cs+].[Cs+]>C(OCC)(=O)C>[C:30]([C:8]1[N:9]=[C:10]([CH2:28][CH3:29])[C:11]([O:13][C:14]2[CH:15]=[C:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:17]=[CH:18][CH:19]=2)=[N:12][C:7]=1[O:6][C:5]1[CH:33]=[CH:34][C:2]([C:39]2[CH2:40][CH2:41][N:36]([CH3:35])[CH2:37][CH:38]=2)=[CH:3][CH:4]=1)(=[O:32])[NH2:31]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 207733711-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridineHCID 117675489HCID 117675489, 화합물

생성물 1

HCID 117675490HCID 117675490, 화합물수율 27.5%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of tert-butyl (3-{[6-(4-bromophenoxy)-5-carbamoyl-3-ethylpyrazin-2-yl]oxy}phenyl)carbamate (540 mg), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine (273 mg), and N,N-dimethylformamide (10 mL) were added a 1,1′-bis(diphenylphosphino)ferrocene palladium (II) dichloride-dichloromethane complex (83 mg) and cesium carbonate (665 mg), followed by reacting at 80° C. for 1 hour. The reaction mixture was left to be cooled, and then ethyl acetate was added thereto. The mixture was washed with water and saturated brine and dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=1:0-9:1) and silica gel column chromatography (NH2 type, eluent; chloroform:methanol=100:0-98:2) to obtain tert-butyl [3-({5-carbamoyl-3-ethyl-6-[4-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)phenoxy]pyrazin-2-yl}oxy)phenyl]carbamate (153 mg) as a pale yellow oily substance.

후처리

  1. waitThe reaction mixture was left
  2. temperatureto be cooled
  3. washThe mixture was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=1:0-9:1) and silica gel column chromatography (NH2 type, eluent; chloroform:methanol=100:0-98:2)

출처 및 근거

ORD 기록
ord-f58dff83c3a2483fb9ee9de03088c37b
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085540B2

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