Pyridine → HCID 67253818, compound

HRID 1711690Notes

Reaction equation

HRID 1711690 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[C:14]([NH2:15])=[CH:13][C:12]([CH:16]([CH3:18])[CH3:17])=[N:11]3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.N1C=CC=CC=1.[C:25](Cl)([O:27][CH2:28][C:29]([Cl:32])([Cl:31])[Cl:30])=[O:26]>C(Cl)Cl>[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[C:14]([NH:15][C:25](=[O:26])[O:27][CH2:28][C:29]([Cl:32])([Cl:31])[Cl:30])=[CH:13][C:12]([CH:16]([CH3:18])[CH3:17])=[N:11]3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 67253832HCID 67253832, compound

Product 1

HCID 67253818HCID 67253818, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 1-(benzo[d]thiazol-6-yl)-3-isopropyl-1H-pyrazol-5-amine (0.80 g, 3.1 mmol) and pyridine (0.51 ml, 6.2 mmol) in CH2Cl2 (30 ml) at RT was added Troc-Cl (0.51 ml, 3.7 mmol). After 2 h, the completed reaction was washed with 10% CuSO4 (2×), H2O (1×), brine (1×), dried (MgSO4), evaporated and purified by flash column chromatography (EtOAc/hexanes) to afford 2,2,2-trichloroethyl 1-(benzo[d]thiazol-6-yl)-3-isopropyl-1H-pyrazol-5-ylcarbamate (0.31 g, 23% yield) as an oil. MS (ESI) m/z: 433.0 (M+H+), 435.0 (M+2+H+).

Workup

  1. customthe completed reaction
  2. washwas washed with 10% CuSO4 (2×), H2O (1×), brine (1×)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. custompurified by flash column chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-5bbb3f79cdf44b6298d5ca54bd0706fe
Source dataset
uspto-grants-2010_09
Patent number
US07790756B2

Reaction notes

Loading…