Ammonium Hydroxide → Tert-butyl ((6-bromothiazolo[5,4-b]pyridin-2-yl)methyl)carbamate

HRID 1487535노트

반응식

HRID 1487535 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([CH2:11]Br)[S:8][C:5]2=[N:6][CH:7]=1.[OH-].[NH4+:14].[CH3:15][C:16]([O:19][C:20]([O:22]C(OC(C)(C)C)=O)=O)([CH3:18])[CH3:17]>O1CCCC1.C([O-])(O)=O.[Na+]>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([CH2:11][NH:14][C:20](=[O:22])[O:19][C:16]([CH3:18])([CH3:17])[CH3:15])[S:8][C:5]2=[N:6][CH:7]=1

참가 물질

6

반응물 3

HCID 14923Ammonium HydroxideHCID 90495Di-tert-butyl dicarbonateHCID 594027536-Bromo-2-(bromomethyl)thiazolo[5,4-b]pyridine

생성물 1

HCID 86695489Tert-butyl ((6-bromothiazolo[5,4-b]pyridin-2-yl)methyl)carbamate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution 6-bromo-2-(bromomethyl)thiazolo[5,4-b]pyridine (800 mg, 2.60 mmol) (Journal of Medicinal Chemistry, 53(10), 3927-3936; 2010) in tetrahydrofuran (10 mL) is added ammonium hydroxide (2 mL) and stirred at room temperature for 16 hours. Reaction is concentrated, diluted with water (5 mL) and extracted using ethyl acetate (3×10 ml). Extracts are dried over Na2SO4 and concentrated to get crude product (650 mg). m/z (CI) M+244. To a solution of crude amine (350 mg, 1.43 mmol) in tetrahydrofuran (10 mL) and aqueous NaHCO3 (2 mL) is added boc anhydride and resulting mixture stirred at room temperature for over night. Organic solution is separated and aqueous layer extracted with ethyl acetate (5 mL). Combined organic solution is dried over Na2SO4 and concentrated under vacuum to give the title compound (400 mg): 1H NMR (400 MHz, CDCl3) 1.50 (s, 9H), 4.74 (d, 2H), 8.36 (s, 1H), 8.62 (s, 1H). m/z (CI) M+2 346.

후처리

  1. customReaction
  2. concentrationis concentrated
  3. additiondiluted with water (5 mL)
  4. extractionextracted
  5. dry with materialExtracts are dried over Na2SO4
  6. concentrationconcentrated
  7. customto get crude product (650 mg)
  8. customresulting mixture
  9. stirringstirred at room temperature for over night
  10. customOrganic solution is separated
  11. extractionaqueous layer extracted with ethyl acetate (5 mL)
  12. dry with materialCombined organic solution is dried over Na2SO4
  13. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-7c99ab48b4c24de29f84a01d692dd803
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428528B2

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