Potassium Phosphate, Tribasic → Pyridin-3-ylmethyl{[4-({[6-chloro-3-({[(1,1-dimethylethyl)oxy]carbonyl}amino)pyridin-2-yl]amino}carbonyl)phenyl]methyl}carbamate

HRID 1256658노트

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HRID 1256658 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][O:8][C:9](=[O:21])[NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([NH2:20])=[O:19])=[CH:14][CH:13]=2)[CH:2]=1.CC([N:26]([C:30]1[C:31](Cl)=[N:32][C:33]([Cl:36])=[CH:34][CH:35]=1)[C:27](=[O:29])[O-:28])(C)C.[CH3:38][C:39]1(C)[C:65]2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=C[C:40]1=2.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C(OCC)(=O)C.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]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][O:8][C:9](=[O:21])[NH:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]([NH:20][C:31]3[C:30]([NH:26][C:27]([O:28][C:39]([CH3:65])([CH3:40])[CH3:38])=[O:29])=[CH:35][CH:34]=[C:33]([Cl:36])[N:32]=3)=[O:19])=[CH:16][CH:17]=2)[CH:2]=1

참가 물질

8

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 57745589HCID 57745589, 화합물HCID 1317306211,1-Dimethylethyl(2,6-dichloropyridin-3-yl)carbamate

생성물 1

HCID 59627859Pyridin-3-ylmethyl{[4-({[6-chloro-3-({[(1,1-dimethylethyl)oxy]carbonyl}amino)pyridin-2-yl]amino}carbonyl)phenyl]methyl}carbamate

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

A solution of pyridin-3-ylmethyl{[4-(aminocarbonyl)phenyl]methyl}carbamate (0.2 g, 0.70 mmol), 1,1-dimethylethyl(2,6-dichloropyridin-3-yl)carbamate (0.18 g, 0.70 mmol), Pd2(dba)3 (32 mg, 0.035 mmol), Xantphos (41 mg, 0.07 mmol) and K3PO4 (0.45 g, 2.1 mmol) in dioxane (3 mL) was degassed with nitrogen, sealed and heated to 100° C. for 14 hours. The reaction was diluted with ethyl acetate (50 mL), filtered through Celite and evaporated in vacuo. Purification by flash chromatography (0-3% methanol/DCM) gave pyridin-3-ylmethyl{[4-({[6-chloro-3-({[(1,1-dimethylethyl)oxy]carbonyl}amino)pyridin-2-yl]amino}carbonyl)phenyl]methyl}carbamate. MS: cal'd 512 (MH+), exp 512 (MH+).

후처리

  1. customsealed
  2. filtrationfiltered through Celite
  3. customevaporated in vacuo
  4. customPurification by flash chromatography (0-3% methanol/DCM)

출처 및 근거

ORD 기록
ord-a860497769c34f648926b060c6442e18
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461189B2

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