3-Aminopyridine → 2-(2-(5-Chloro-2-(pyridin-3-ylamino)pyrimidin-4-ylethyl)phenyl)propanamide

HRID 592420노트

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HRID 592420 반응식
[Cl:1][C:2]1[C:3]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH:23]([CH3:27])[C:24]([NH2:26])=[O:25])=[N:4][C:5]([NH:8][C:9]2[CH:10]=N[N:12]([CH3:14])[CH:13]=2)=[N:6][CH:7]=1.N[C:29]1C=NC=CC=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.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[C:3]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH:23]([CH3:27])[C:24]([NH2:26])=[O:25])=[N:4][C:5]([NH:8][C:9]2[CH:13]=[N:12][CH:14]=[CH:29][CH:10]=2)=[N:6][CH:7]=1

참가 물질

7

반응물 4

HCID 100093-AminopyridineHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 732972072-(2-(5-chloro-2-(1-methyl-1H-pyrazol-4-ylamino)pyrimidin-4-ylethyl)phenyl)propanamide

생성물 1

HCID 732972102-(2-(5-Chloro-2-(pyridin-3-ylamino)pyrimidin-4-ylethyl)phenyl)propanamide수율 31%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

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온도
120 °C

실험 절차

A mixture of 2-(2-(2-(5-chloro-2-(1-methyl-1H-pyrazol-4-ylamino)pyrimidin-4-ylethyl)phenyl)propanamide A30 (0.080 g, 0.25 mmol), 3-aminopyridine (0.046 g, 0.49 mmol), Xantphos (0.0057 g, 0.010 mmol) and Cs2CO3 (0.24 g, 0.74 mmol) in 1,4-dioxane (3 mL) was bubbled with nitrogen for 10 minutes. Palladium (II) acetate (0.0011 g, 0.0049 mmol) was added and the mixture was heated at 120° C. under microwave irradiation for 28 minutes. The volatiles were removed in vacuo and the residue was purified by silica gel column chromatography (Combiflash Rf, 0-10% MeOH in DCM) to give the title compound 39 as a pink solid (0.029 g, 31%). LCMS-C: rt 4.30 min; m/z 382 [M+H]+.

후처리

  1. customwas bubbled with nitrogen for 10 minutes
  2. customThe volatiles were removed in vacuo
  3. customthe residue was purified by silica gel column chromatography (Combiflash Rf, 0-10% MeOH in DCM)

출처 및 근거

ORD 기록
ord-9be0dae21c004756a55ea18718714018
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238644B2

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