Hydrochloric Acid → Tert-butyl 5-amino-2-chloropyridin-3-ylcarbamate

HRID 1812420

반응식

HRID 1812420 반응식
[Cl:1][C:2]1[C:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][C:5]([N:16]=C(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:4][N:3]=1.Cl>C1COCC1>[NH2:16][C:5]1[CH:6]=[C:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:12])[CH3:14])[C:2]([Cl:1])=[N:3][CH:4]=1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 86647087Tert-butyl 2-chloro-5-(diphenylmethyleneamino)pyridin-3-ylcarbamate

생성물 1

HCID 86647086Tert-butyl 5-amino-2-chloropyridin-3-ylcarbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of tert-butyl 2-chloro-5-(diphenylmethyleneamino)pyridin-3-ylcarbamate (0.280 g, 0.686 mmol) in THF (5 mL) was added hydrochloric acid, In (JT Baker) (0.031 mL, 1.030 mmol). The reaction was stirred at rt in closed system for 20 min. The reaction mixture was partitioned between EtOAc/sat. NaHCO3. The aqueous layer was extracted with EtOAc (2×10 mL). The combined organic layer were dried over MgSO4 and concentrated. The crude product was purified by column chromatography (24 g, 3% MeOH in DCM) to afford the desired product as a white foam-like solid (135.0 mg). MS (ESI pos. ion) m/z: 244.1. 1H NMR (300 MHz, CDCl3) δ ppm 1.54 (s, 9H) 3.73 (br. s., 2H) 6.93 (br. s., 1H) 7.52 (d, J=2.63 Hz, 1H) 7.94 (d, J=2.63 Hz, 1H).

후처리

  1. customThe reaction mixture was partitioned between EtOAc/
  2. extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
  3. dry with materialThe combined organic layer were dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (24 g, 3% MeOH in DCM)

출처 및 근거

ORD 기록
ord-464db90757bd406b9a26e60b36b7bf28
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362241B2

연결된 노트

불러오는 중…