Sodium Carbonate → N-(4-(6-(5-methylthiazol-2-ylamino)pyrazin-2-ylthio)phenyl)cyclopropanecarboxamide

HRID 1668651

반응식

HRID 1668651 반응식
Cl[C:2]1[N:7]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])=[CH:11][CH:10]=2)[CH:5]=[N:4][CH:3]=1.[NH2:21][C:22]1[S:23][C:24]([CH3:27])=[CH:25][N:26]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>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].C(OCC)(=O)C.O>[CH3:27][C:24]1[S:23][C:22]([NH:21][C:2]2[N:7]=[C:6]([S:8][C:9]3[CH:14]=[CH:13][C:12]([NH:15][C:16]([CH:18]4[CH2:20][CH2:19]4)=[O:17])=[CH:11][CH:10]=3)[CH:5]=[N:4][CH:3]=2)=[N:26][CH:25]=1

참가 물질

9

반응물 4

HCID 10340Sodium CarbonateHCID 3517702-Amino-5-methylthiazoleHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 59343401N-(4-(6-chloropyrazin-2-ylthio)phenyl)cyclopropanecarboxamide

생성물 1

HCID 15950453N-(4-(6-(5-methylthiazol-2-ylamino)pyrazin-2-ylthio)phenyl)cyclopropanecarboxamide수율 14%

시약·촉매·용매 4

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

To a solution of N-(4-(6-chloropyrazin-2-ylthio)phenyl)cyclopropanecarboxamide (0.82 mmol) and 2-amino-5-methylthiazole (0.86 mmol) in 1,4-dioxan (3 mL), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.05 mmol), tris(dibenzylideneacetone)dipalladium (0.03 mmol) and sodium carbonate (1.15 mmol) were added. The resulting solution was heated at 120° C. in the microwave (175W, 25 psi) for 3 h. Water (10 mL) and ethyl acetate (10 mL) were added and the layers separated. The aqueous layer was extracted further with ethyl acetate (2×10 mL), the combined organic layers dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography eluting with MeOH:CH2Cl2 (1:20) to give the title compound (42.5 mg, 14%) as a light brown solid; 1H NMR (400 MHz, DMSO-d6) δ 0.81 (4H, m), 1.82 (1H, m), 2.16 (3H, s), 3.32 masked signal, 6.99 (1H, m), 7.58 (2H, m), 7.76 (2H, m), 7.84 (1H, s), 8.04 (1H, s), 10.49 (1H, s), 11.50 (1H, br s); MS (ES+): m/e=384.48 (100%).

후처리

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted further with ethyl acetate (2×10 mL)
  3. dry with materialthe combined organic layers dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography
  6. washeluting with MeOH:CH2Cl2 (1:20)

출처 및 근거

ORD 기록
ord-8ac961623cde446f88d676824e143df1
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989456B2

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