Potassium Carbonate → 5-(Pyridin-2-ylsulfanyl)-thiazol-2-ylamine

HRID 852931노트

반응식

HRID 852931 반응식
Br.[NH2:2][C:3]1[S:4][C:5](Br)=[CH:6][N:7]=1.[SH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[S:9][C:5]1[S:4][C:3]([NH2:2])=[N:7][CH:6]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 27238485-Bromothiazol-2-amine monohydrobromideHCID 178418616HCID 178418616, 화합물

생성물 1

HCID 157291575-(Pyridin-2-ylsulfanyl)-thiazol-2-ylamine수율 73.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a solution of 2-amino-5-bromothiazole hydrobromide (1.00 g, 3.85 mmol) in DMF (8 mL) was added 2-mercaptopyridine (428 mg, 3.85 mmol) followed by addition of powdered K2CO3 (1.81 g, 15.09 mmol). The mixture was stirred at 80° C. for 1 h and at rt for 16 h. The solvent was removed in vacuo at 80° C. and the compound was partitioned between H2O and EtOAc. The aqueous layer was extracted with EtOAc and the organic phase was extracted with HCl 1N. The acidic extract was neutralized with saturated NaHCO3 and the precipitate was extracted with EtOAc, washed with brine, dried over MgSO4 and concentrated in vacuo to afford the title compound 169 (589 mg, 73% yield). 1H NMR: (Acetone-d6) δ (ppm): 8.36 (s, 1H), 7.66 (s, 1H), 7.20 (s, 1H), 7.12-7.05 (m, 2H), 6.84 (s, 2H). m/z: 210.1 (MH+).

후처리

  1. customThe solvent was removed in vacuo at 80° C.
  2. customthe compound was partitioned between H2O and EtOAc
  3. extractionThe aqueous layer was extracted with EtOAc
  4. extractionthe organic phase was extracted with HCl 1N
  5. extractionThe acidic extract
  6. extractionthe precipitate was extracted with EtOAc
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a818b4a0887446f3a8197bf14d7e7f08
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253204B2

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