Potassium Phosphate, Tribasic → Ethyl 5-[(tert-butoxycarbonyl)amino]-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxylate

HRID 2060631노트

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HRID 2060631 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][C:12](I)=[N:11][C:10]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC1(C)C(C)(C)OB([C:28]2[CH:29]=[CH:30][C:31]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[N:32][CH:33]=2)O1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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].O1CCOCC1>[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][C:12]([C:28]2[CH:33]=[N:32][C:31]([N:34]3[CH2:35][CH2:36][O:37][CH2:38][CH2:39]3)=[CH:30][CH:29]=2)=[N:11][C:10]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

8

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 27953634-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl)morpholineHCID 67306268Ethyl 5-((tert-butoxycarbonyl)amino)-2-iodothiazole-4-carboxylate

생성물 1

HCID 67305664Ethyl 5-[(tert-butoxycarbonyl)amino]-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxylate

시약·촉매·용매 3

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

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온도
100 °C

실험 절차

Ethyl 5-[(tert-butoxycarbonyl)amino]-2-iodo-1,3-thiazole-4-carboxylate (1 g, 2.5 mmol), 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]morpholine (1.1 g, 3.7 mmol), Pd2(dba)3 (0.23 g, 0.25 mmol), and tricyclohexylphosphine (0.18 g, 0.63 mmol) were combined in a flask. The flask was evacuated and backfilled with argon three times. Fully degassed dioxane (17 mL) and 1.27 M aqueous potassium phosphate (6.5 ml, 8.3 mmol) were added sequentially. The reaction was heated to 100° C. for 6 h. The mixture was then cooled, diluted with ethyl acetate, washed with water, dried (MgSO4), filtered, and the solvent was evaporated under reduced pressure. The resulting residue was purified by flash chromatography (silica, 0-75% ethyl acetate/hexanes) to afford the title compound as a yellow solid. LRMS (APCI) calc'd for (C20H27N4O5S) [M+H]+, 435.2; found 435.0.

후처리

  1. customThe flask was evacuated
  2. temperatureThe mixture was then cooled
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customThe resulting residue was purified by flash chromatography (silica, 0-75% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-1a16f5ae51f743eeb9fc462ff535fc49
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08278335B2

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