Cesium carbonate → 6-Chloro-4-(5-(methoxymethyl)-1-methyl-1H-pyrazol-3-ylamino)-2-methylpyridazin-3(2H)-one

HRID 1918955노트

반응식

HRID 1918955 반응식
BrC1C=C([NH:10][C:11]2[CH:15]=[C:14]([CH2:16][O:17][CH3:18])[N:13]([CH3:19])[N:12]=2)C(=O)N(C)C=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.Br[C:63]1[C:64](=[O:71])[N:65]([CH3:70])[N:66]=[C:67]([Cl:69])[CH:68]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:69][C:67]1[CH:68]=[C:63]([NH:10][C:11]2[CH:15]=[C:14]([CH2:16][O:17][CH3:18])[N:13]([CH3:19])[N:12]=2)[C:64](=[O:71])[N:65]([CH3:70])[N:66]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 580441025-Bromo-3-(5-(methoxymethyl)-1-methyl-1H-pyrazol-3-ylamino)-1-methylpyridin-2(1H)-oneHCID 592164744-Bromo-6-chloro-2-methyl-2,3-dihydropyridazin-3-one

생성물 1

HCID 580438316-Chloro-4-(5-(methoxymethyl)-1-methyl-1H-pyrazol-3-ylamino)-2-methylpyridazin-3(2H)-one수율 94%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

실험 절차

A mixture of 5-(methoxymethyl)-1-methyl-1H-pyrazol-3-amine 176b (600 mg, 4.26 mmol), XantPhos (300 mg, 0.51 mmol), Pd2 dba3 (310 mg, 0.34 mmol), 4-bromo-6-chloro-2-methylpyridazin-3(2H)-one (103e) (1.22 g, 5.53 mmol) and Cs2CO3 (4.2 g. 12.8 mmol) in 1,4-dioxane (40 mL) was heated at reflux for 2 h. After the completion of the reaction, the mixture was filtered off and washed with methanol (100 mL). The filtrate was evaporated in vacuo and the residue was purified on reverse phase Combi-flash to give 187a (1.13 g, 94%). MS: [M+H]+ 284.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. customAfter the completion of the reaction
  4. filtrationthe mixture was filtered off
  5. washwashed with methanol (100 mL)
  6. customThe filtrate was evaporated in vacuo
  7. customthe residue was purified on reverse phase Combi-flash

출처 및 근거

ORD 기록
ord-d9c3a43ab6a3499ea1d3bc559952f5d4
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618107B2

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