Cesium carbonate → 1-(2-Hydroxyethyl)-3-(5-(2-(2-hydroxypropan-2-yl)pyrimidin-5-yl)-7-(pyridin-2-yl)benzo[d]thiazol-2-yl)urea

HRID 1399992노트

반응식

HRID 1399992 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[N:11][C:12]([C:15]([OH:18])([CH3:17])[CH3:16])=[N:13][CH:14]=2)O1.[OH:20][CH2:21][CH2:22][NH:23][C:24]([NH:26][C:27]1[S:28][C:29]2[C:35]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=3)=[CH:34][C:33](OS(C(F)(F)F)(=O)=O)=[CH:32][C:30]=2[N:31]=1)=[O:25].C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[OH:20][CH2:21][CH2:22][NH:23][C:24]([NH:26][C:27]1[S:28][C:29]2[C:35]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=3)=[CH:34][C:33]([C:9]3[CH:14]=[N:13][C:12]([C:15]([OH:18])([CH3:16])[CH3:17])=[N:11][CH:10]=3)=[CH:32][C:30]=2[N:31]=1)=[O:25]

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 665203402-[5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl]propan-2-olHCID 86696902[2-(2-Hydroxyethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]trifluoromethanesulfonate

생성물 1

HCID 717653401-(2-Hydroxyethyl)-3-(5-(2-(2-hydroxypropan-2-yl)pyrimidin-5-yl)-7-(pyridin-2-yl)benzo[d]thiazol-2-yl)urea

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

To a solution of iii (165 mg, 0.626 mmol) in 1,4-dioxane (12 mL) was added ii (193 mg, 0.417 mmol) and PdCl2(dppf) (34 mg, 0.042 mmol). A solution of Cs2CO3 (410 mg, 1.30 mmol) in H2O (3 mL) was added, the reaction vessel sealed, then evacuated/purged with argon (×3). The mixture was then heated under microwave irradiation at 100° C. for 30 min. LCMS analysis indicated complete conversion. The mixture was diluted with EtOAc (100 mL), washed with H2O, brine, then separated and dried (Na2SO4). The organic fraction was concentrated in vacuo. Purification by chromatography on silica, eluting with 0-10% MeOH/EtOAc followed by additional chromatography on silica, eluting with 0-10% MeOH/DCM afforded Compound 5 (9 mg, 5%).

후처리

  1. customthe reaction vessel sealed
  2. customevacuated/purged with argon (×3)
  3. additionThe mixture was diluted with EtOAc (100 mL)
  4. washwashed with H2O, brine
  5. customseparated
  6. dry with materialdried (Na2SO4)
  7. concentrationThe organic fraction was concentrated in vacuo
  8. customPurification by chromatography on silica
  9. washeluting with 0-10% MeOH/EtOAc
  10. washeluting with 0-10% MeOH/DCM afforded Compound 5 (9 mg, 5%)

출처 및 근거

ORD 기록
ord-a8f280cfc75b42639d051669daf9b35c
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08906902B2

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