Trifluoroacetic acid → HCID 58207992, compound

HRID 2197545Notes

Reaction equation

HRID 2197545 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[S:13][C:12]([NH:14][CH:15]([CH3:17])[CH3:16])=[N:11][CH:10]=2)[CH:5]=[N:6][C:7]=1Cl.O.[NH2:19][NH2:20].[CH:21](OC)(OC)OC.C(O)(C(F)(F)F)=O>CCCCO.C(Cl)Cl>[Br:1][C:2]1[C:7]2[N:6]([CH:21]=[N:19][N:20]=2)[CH:5]=[C:4]([C:9]2[S:13][C:12]([NH:14][CH:15]([CH3:17])[CH3:16])=[N:11][CH:10]=2)[CH:3]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 9005Trimethyl orthoformateHCID 24654Hydrazine hydrate (1:1)HCID 58207927HCID 58207927, compound

Product 1

HCID 58207992HCID 58207992, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
105 °C

Procedure

To a mixture of 5-(5-bromo-6-chloropyridin-3-yl)-N-isopropylthiazol-2-amine (341 mg, 1.02 mmol) in n-BuOH (5 mL) was added hydrazine monohydrate (806 μL, 2.55 mmol). The reaction mixture was heated at 105° C. in a sealed tube overnight, cooled and concentrated. The residue was added trimethyl orthoformate (335 μL, 3.06 mmol), CH2Cl2 (5 mL) and stirred for 10 mins, then added TFA (118 μL, 1.53 mmol). The reaction was continued to stir for 45 mins, and then concentrated. The residue was added water (10 mL), neutralized with NaHCO3, stirred overnight, filtered and rinsed with water. The dried solid was purified by a flash column using 5% MeOH in dichloromethane as an eluent. The product containing fractions were concentrated to give the product (208.1 mg, 60% yield in two-step).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. stirringto stir for 45 mins
  4. concentrationconcentrated
  5. additionThe residue was added water (10 mL)
  6. stirringstirred overnight
  7. filtrationfiltered
  8. washrinsed with water
  9. customThe dried solid was purified by a flash column
  10. additionThe product containing fractions
  11. concentrationwere concentrated
  12. customto give the product (208.1 mg, 60% yield in two-step)

Sources & evidence

ORD record
ord-32ff2c91a51348b5a748dd6c64270122
Source dataset
uspto-grants-2012_12
Patent number
US08338604B2

Reaction notes

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