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

HRID 2366239Notes

Reaction equation

HRID 2366239 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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+].

Workup

  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

Sources & evidence

ORD record
ord-826931338b7e4c5cbee696027638520c
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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