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

HRID 2366239ノート

反応式

HRID 2366239 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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+].

後処理

  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

出典と根拠

ORDレコード
ord-826931338b7e4c5cbee696027638520c
出典データセット
uspto-grants-2014_04
特許番号
US08697708B2

反応ノート

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