Potassium bisulfate → N-Cyclopropyl-4-fluoro-3-[2-(pyridin-2-ylamino)-thiazol-5-ylmethoxy]-benzamide

HRID 6871

Reaction equation

HRID 6871 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[F:14])[C:5]([NH:7][CH:8]1[CH2:10][CH2:9]1)=[O:6].Cl.Cl[CH2:17][C:18]1[S:22][C:21]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=[N:20][CH:19]=1.OS([O-])(=O)=O.[K+]>CN(C=O)C>[CH:8]1([NH:7][C:5](=[O:6])[C:4]2[CH:11]=[CH:12][C:13]([F:14])=[C:2]([O:1][CH2:17][C:18]3[S:22][C:21]([NH:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)=[N:20][CH:19]=3)[CH:3]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 516920Potassium bisulfateHCID 220191063-hydroxy-4-fluoro-N-cyclopropylbenzamideHCID 86591883(5-Chloromethylthiazol-2-yl)pyridin-2-ylamine hydrochloride

Product 1

HCID 22019135N-Cyclopropyl-4-fluoro-3-[2-(pyridin-2-ylamino)-thiazol-5-ylmethoxy]-benzamideYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of NaR (16 mg, 60% in oil) in DMF (1 mL) was added a solution of 3-hydroxy-4-fluoro-N-cyclopropylbenzamide (58.5 mg, 0.3 mmol) in DMF (1 mL) at RT. After 10 min, (5-chloromethylthiazol-2-yl)pyridin-2-ylamine hydrochloride (Example 10A) (52.4 mg, 0.2 mmol) was added. The mixture was stirred at RT for 1 h and poured onto ice. The mixture was neutralized with 1 N KHSO4 solution and the precipitates were collected, washed with water and ethyl acetate to give the title compound as a light yellow solid (25.2 mg, 33%). MS m/z 385 (M+H)+.

Workup

  1. additionpoured onto ice
  2. customthe precipitates were collected
  3. washwashed with water and ethyl acetate

Sources & evidence

ORD record
ord-87002b9f196d4b4bafaff983bc899b02
Source dataset
uspto-grants-2006_08
Patent number
US07084160B2

Linked notes

Loading…