3,4,5-Trimethoxybenzylamine → HCID 67983329, 화합물

HRID 539801

반응식

HRID 539801 반응식
Cl[C:2]1[CH:7]=[CH:6][C:5]2=[N:8][C:9]([C:11]3[CH:12]=[CH:13][C:14]([CH3:24])=[C:15]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=3)=[CH:10][N:4]2[N:3]=1.CC(C1C=C(C(C)C)C(C2C(P(C(C)(C)C)C(C)(C)C)=CC=CC=2)=C(C(C)C)C=1)C.CC(C)([O-])C.[Na+].[CH3:61][O:62][C:63]1[CH:64]=[C:65]([CH:68]=[C:69]([O:73][CH3:74])[C:70]=1[O:71][CH3:72])[CH2:66][NH2:67]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1(C)C=CC=CC=1>[CH3:24][C:14]1[CH:13]=[CH:12][C:11]([C:9]2[N:8]=[C:5]3[CH:6]=[CH:7][C:2]([NH:67][CH2:66][C:65]4[CH:68]=[C:69]([O:73][CH3:74])[C:70]([O:71][CH3:72])=[C:63]([O:62][CH3:61])[CH:64]=4)=[N:3][N:4]3[CH:10]=2)=[CH:16][C:15]=1[NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20]

참가 물질

7

반응물 4

HCID 877363,4,5-TrimethoxybenzylamineHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneHCID 23676156Sodium t-butoxideHCID 86667859HCID 86667859, 화합물

생성물 1

HCID 67983329HCID 67983329, 화합물수율 40%

시약·촉매·용매 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

A 40-mL vial is charged with N-[5-(6-chloroimidazo[2,1-f]pyridazin-2-yl)-2-methyl-phenyl]-2,2-dimethyl-propanamide (1.0285 g, 3 mmol), tert-butyl xphos (0.255 g, 0.6 mmol), sodium tert-butoxide (0.577 g, 6 mmol), and bis(dibenzylideneacetone)palladium(0) (0.172 g, 0.3 mmol) and the vial is purged with N2. Toluene (16 mL) and 3,4,5-trimethoxybenzylamine (1.54 mL, 9 mmol) is added and the mixture heated at 100° C. for 1 hr. The reaction mixture is filtered through celite, washed with 1:1:0.1 CH2Cl2:EtOAc:MeOH and concentrated onto celite, and purified by silica gel chromatography (0-100% 1:1:0.1 CH2Cl2:EtOAc:MeOH) to afford the title compound (0.604 g). LCMS (m/z)=504.6 [M+H]+, tR=2.31 min.

후처리

  1. customthe vial is purged with N2
  2. filtrationThe reaction mixture is filtered through celite
  3. washwashed with 1:1:0.1 CH2Cl2
  4. concentrationEtOAc:MeOH and concentrated onto celite
  5. custompurified by silica gel chromatography (0-100% 1:1:0.1 CH2Cl2:EtOAc:MeOH)

출처 및 근거

ORD 기록
ord-1907d305fbb24cd69e53c2d20a983f05
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871767B2

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