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Cesium carbonate → (2-Methyl-7-pyridin-3-yl-thiazolo[4,5-c]pyridin-4-yl)-(2-methyl-thiazol-4-yl)-amine

HRID 1443084
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HRID 1443084 반응식
Cl[C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[S:10][C:6]=2[C:5]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[CH:4][N:3]=1.[NH2:18][C:19]1[N:20]=[C:21]([CH3:24])[S:22][CH:23]=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-].[Cs+].[Cs+]>O1CCOCC1>[CH3:11][C:9]1[S:10][C:6]2[C:5]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)=[CH:4][N:3]=[C:2]([NH:18][C:19]3[N:20]=[C:21]([CH3:24])[S:22][CH:23]=3)[C:7]=2[N:8]=1
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참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 147727002-Methyl-1,3-thiazol-4-amineHCID 866124154-Chloro-2-methyl-7-pyridin-3-yl-thiazolo[4,5-c]pyridine

생성물 1

HCID 16660577(2-Methyl-7-pyridin-3-yl-thiazolo[4,5-c]pyridin-4-yl)-(2-methyl-thiazol-4-yl)-amine

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

4-Chloro-2-methyl-7-pyridin-3-yl-thiazolo[4,5-c]pyridine (100 mg, 0.38 mmol) and 4-amino-2-methylthiazole (44 mg, 0.38 mmol) (Example C) were dissolved in 3 ml dry dioxane. 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (44 mg, 0.08 mmol) and cesium carbonate (200 mg, 0.61 mmol) were added and this mixture was evacuated and backfilled with argon several times to remove oxygen from the solution. Tris(dibenzylideneacetone)dipalladium chloroform complex (38 mg, 0.035 mmol) was added and the reaction mixture was stirred for 1 hour at 100° C. The reaction mixture was then evaporated and purified by flash chromatography on silica gel (heptane/ethyl acetate 90:10->0:100 gradient) and recrystallization in diisopropylether. The desired product was obtained as a yellow solid (20 mg, 15%), MS: m/e 354.1 (M+H+).

후처리

  1. customthis mixture was evacuated
  2. customto remove oxygen from the solution
  3. additionTris(dibenzylideneacetone)dipalladium chloroform complex (38 mg, 0.035 mmol) was added
  4. customThe reaction mixture was then evaporated
  5. custompurified by flash chromatography on silica gel (heptane/ethyl acetate 90:10->0:100 gradient) and recrystallization in diisopropylether

출처 및 근거

ORD 기록
ord-e27c29bee49b45af9edf22c6e14e31cf
출처 데이터셋
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07659401B2

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