Piperazine → 6-(4-(2-fluorophenyl)-1H-imidazol-5-yl)-N-isopropylthiazolo[4,5-c]pyridin-2-amine

HRID 1452971노트

반응식

HRID 1452971 반응식
[CH:1]([NH:4][C:5]1[S:6][C:7]2[CH:12]=[C:11]([CH:13]=O)[N:10]=[CH:9][C:8]=2[N:15]=1)([CH3:3])[CH3:2].[NH4+].[OH-].[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH:25]([N+:36]#[C-:37])S(C1C=CC(C)=CC=1)(=O)=O.[NH:38]1CCNCC1>C1COCC1.CCOC(C)=O>[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[N:36]=[CH:37][NH:38][C:13]=1[C:11]1[N:10]=[CH:9][C:8]2[N:15]=[C:5]([NH:4][CH:1]([CH3:3])[CH3:2])[S:6][C:7]=2[CH:12]=1

참가 물질

7

반응물 4

HCID 4837PiperazineHCID 14923Ammonium HydroxideHCID 467382311-Fluoro-2-(isocyano(tosyl)methyl)benzeneHCID 575272142-(Isopropylamino)thiazolo[4,5-c]pyridine-6-carbaldehyde

생성물 1

HCID 159874876-(4-(2-fluorophenyl)-1H-imidazol-5-yl)-N-isopropylthiazolo[4,5-c]pyridin-2-amine수율 25%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 2-(isopropylamino)thiazolo[4,5-c]pyridine-6-carbaldehyde (example 10, step 4) (presumed 0.244 mmol, 1.0 eq.) and concentrated aqueous NH4OH (0.050 mL) in THF (1 mL) was stirred overnight. 1-Fluoro-2-(isocyano(tosyl)methyl)benzene (0.0880 g, 0.304 mmol, 1.2 eq.) and piperazine (0.0371 g, 0.431 mmol, 1.8 eq.) were added, and the reaction mixture was stirred overnight. It was then diluted with EtOAc and washed with water, saturated aqueous NaHCO3, and brine, dried over Na2SO4, filtered, and concentrated in vacuo. MeOH was added to the residue, and the mixture was subjected to autoprep. The appropriate fractions were collected, and NaHCO3 (s) was added. The solution was then concentrated in vacuo not to dryness and extracted with EtOAc (3×). The organic layers were combined, dried over Na2SO4, filtered, and concentrated in vacuo to give 6-(4-(2-fluorophenyl)-1H-imidazol-5-yl)-N-isopropylthiazolo[4,5-c]pyridin-2-amine as a light orange solid (0.0212 g, 25% yield). LC/MS (MH)=354.18.

후처리

  1. washwashed with water, saturated aqueous NaHCO3, and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. additionMeOH was added to the residue
  6. customThe appropriate fractions were collected
  7. additionNaHCO3 (s) was added
  8. concentrationThe solution was then concentrated in vacuo not to dryness
  9. extractionextracted with EtOAc (3×)
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4a65dbdb5a284c458774dfaddf48a8a7
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07473784B2

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