N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-fluorothiazol-2-yl)-6-methylpyridin-2-amine → 5-fluoro-N-(6-methylpyridin-2-yl)-4-(1H-pyrazol-4-yl)thiazol-2-amine

HRID 1520206노트

반응식

HRID 1520206 반응식
COC1C=CC(C[N:8]2[CH:12]=[C:11]([C:13]3[N:14]=[C:15]([NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[N:21]=4)[S:16][C:17]=3[F:18])[CH:10]=[N:9]2)=CC=1>C(O)(C(F)(F)F)=O>[F:18][C:17]1[S:16][C:15]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[N:21]=2)=[N:14][C:13]=1[C:11]1[CH:12]=[N:8][NH:9][CH:10]=1

참가 물질

3

반응물 1

HCID 86658559N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-fluorothiazol-2-yl)-6-methylpyridin-2-amine

생성물 1

HCID 468367265-fluoro-N-(6-methylpyridin-2-yl)-4-(1H-pyrazol-4-yl)thiazol-2-amine수율 50%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

According to Scheme 6 Step 4: A solution of N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-fluorothiazol-2-yl)-6-methylpyridin-2-amine (0.24 mmol, 95 mg) in TFA (3 mL) was microwaved for 8 minutes at 140° C. After evaporation of the solvent, the reaction mixture was neutralized with a solution of NaOH (1 M). The aqueous phase was extracted with DCM and with AcOEt. The organic phase was dried over MgSO4, was filtered and was concentrated. The resulting crude product was washed with Et2O to yield 5-fluoro-N-(6-methylpyridin-2-yl)-4-(1H-pyrazol-4-yl)thiazol-2-amine (0.12 mmol, 33 mg, 50%) as a beige solid.

후처리

  1. customAfter evaporation of the solvent
  2. extractionThe aqueous phase was extracted with DCM and with AcOEt
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationwas filtered
  5. concentrationwas concentrated
  6. washThe resulting crude product was washed with Et2O

출처 및 근거

ORD 기록
ord-c3592a2b046e4334a3a4958cc275bd32
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073907B2

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