Trifluoroacetic acid → 4-(4-Amino-thiazolo[5,4-c]pyridin-2-yl)-3,5-dichloro-benzonitrile

HRID 2366239노트

반응식

HRID 2366239 반응식
C(OC(=O)[NH:7][C:8]1[C:13]2[S:14][C:15]([C:17]3[C:22]([Cl:23])=[CH:21][C:20]([C:24]#[N:25])=[CH:19][C:18]=3[Cl:26])=[N:16][C:12]=2[CH:11]=[CH:10][N:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C:8]1[C:13]2[S:14][C:15]([C:17]3[C:22]([Cl:23])=[CH:21][C:20]([C:24]#[N:25])=[CH:19][C:18]=3[Cl:26])=[N:16][C:12]=2[CH:11]=[CH:10][N:9]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 66801860[2-(2,6-Dichloro-4-cyano-phenyl)-thiazolo[5,4-c]pyridin-4-yl]-carbamic acid tert-butyl ester

생성물 1

HCID 668018504-(4-Amino-thiazolo[5,4-c]pyridin-2-yl)-3,5-dichloro-benzonitrile수율 84.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of [2-(2,6-dichloro-4-cyano-phenyl)-thiazolo[5,4-c]pyridin-4-yl]-carbamic acid tert-butyl ester (0.48 g, 1.14 mmol) and TFA (2 mL) in DCM (8 mL) was stirred at room temperature for 2 hours then concentrated to dryness under reduced pressure. The resultant residue was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M ammonia in isopropanol. The relevant fractions were combined and concentrated under reduced pressure to afford the title compound as a pale yellow solid (0.309 g, 82% yield). 1H NMR (300 MHz, CDCl3): δ 8.21 (d, J=5.8 Hz, 1H), 7.77 (s, 2H), 7.50 (d, J=5.8 Hz, 1H), 4.94 (s, 2H). LCMS (Method D): RT=2.04 min, m/z: 321 [M+H+].

후처리

  1. concentrationthen concentrated to dryness under reduced pressure
  2. washwas washed with MeOH
  3. washthe product eluted with 2M ammonia in isopropanol
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-826931338b7e4c5cbee696027638520c
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697708B2

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