Water → 6-Bromo-2-chlorothiazolo[4,5-b]pyridine hydrochloride

HRID 1429536노트

반응식

HRID 1429536 반응식
Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[C:10]([S-:15])(=S)OCC.[K+].S(Cl)([Cl:20])(=O)=O.O>CN(C=O)C.Cl>[ClH:20].[Br:8][C:6]1[CH:7]=[C:2]2[S:15][C:10]([Cl:20])=[N:9][C:3]2=[N:4][CH:5]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 24648Sulfuryl chloride2회HCID 988513,5-Dibromo-2-pyridylamineHCID 2735045Potassium ethylxanthate

생성물 1

HCID 674627556-Bromo-2-chlorothiazolo[4,5-b]pyridine hydrochloride수율 99%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 6228Dimethylformamide용매

실험 절차

A solution of 3,5-dibromopyridine-2-amine (5 g, 19.85 mmol) and potassium O-ethyl carbonodithioate (7.64 g, 47.6 mmol) in DMF (25.6 mL) was heated to 130° C. where it stirred overnight. After this time, the reaction mixture was allowed to cool to rt. Once at the prescribed temperature, the reaction mixture was diluted with HCl (1 N, 150 mL), and then stirred at rt for an additional hour. At the conclusion of this period, the resulting solid was collected by filtration, washed with water (2×15 mL), and then air-dried. The resulting material was suspended in CH2Cl2 (26 mL) and sulfuryl chloride (17.1 mL, 210 mmol) was slowly added. After 2 hr, water (50 mL) was slowly added to decompose the excess sulfuryl chloride (cooled to 0° C.). The resulting precipitate was collected by filtration and dried to afford Compound 21A as a light yellow solid (5.6 g, 99% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.88 (d, J=2.2 Hz, 1H), 8.79 (d, J=2.2 Hz, 1H). LC/MS (m/z)=250 (M+H)+.

후처리

  1. stirringstirred at rt for an additional hour
  2. filtrationAt the conclusion of this period, the resulting solid was collected by filtration
  3. washwashed with water (2×15 mL)
  4. customair-dried
  5. waitAfter 2 hr
  6. filtrationThe resulting precipitate was collected by filtration
  7. customdried

출처 및 근거

ORD 기록
ord-49f856b585334548b5a7888eb14bee13
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940716B2

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