HCID 66803505, compound → HCID 66801483, compound

HRID 2366245Notes

Reaction equation

HRID 2366245 reaction equation
C(OC(=O)[NH:7][C:8]1[C:13]2[S:14][C:15]([C:17]3[C:22]([F: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>Cl>[NH2:7][C:8]1[C:13]2[S:14][C:15]([C:17]3[C:22]([F: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

3

Reactant 1

HCID 66803505HCID 66803505, compound

Product 1

HCID 66801483HCID 66801483, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of [2-(2-chloro-4-cyano-6-fluorophenyl)thiazolo[5,4-c]pyridin-4-yl]-carbamic acid tert-butyl ester (0.320 mmol) in HCl (4N in dioxane, 2.5 mL) was heated at 50° C. for 3 hours in a sealed vial. After cooling to room temperature, the volatiles were removed under reduced pressure and the resultant residue was partitioned between EtOAc and a saturated solution of NaHCO3. The aqueous phase was extracted with EtOAc, and the combined organic layers were washed with brine, dried (Na2SO4) and concentrated to dryness under reduced pressure to afford the title compound as a yellow solid (76 mg, 78% yield over two steps). 1H NMR (400 MHz, CDCl3): δ 8.21 (d, J=5.8 Hz, 1H), 7.69 (t, J=1.4 Hz, 1H), 7.53-7.46 (m, 2H), 4.84 (s, 2H).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe volatiles were removed under reduced pressure
  3. customthe resultant residue was partitioned between EtOAc
  4. extractionThe aqueous phase was extracted with EtOAc
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-b08098a603394c60a7f96e540ce4ef16
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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