2-Aminothiazole → HCID 58154783, compound

HRID 2359427Notes

Reaction equation

HRID 2359427 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[C:11]([C:18]([OH:20])=O)[CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:5]=[CH:4][N:3]=1.[S:21]1[CH:25]=[CH:24][N:23]=[C:22]1[NH2:26].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[C:11]([C:18]([NH:26][C:22]4[S:21][CH:25]=[CH:24][N:23]=4)=[O:20])[CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 21552-AminothiazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 50990505HCID 50990505, compound

Product 1

HCID 58154783HCID 58154783, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-(2-chloropyridin-4-yl)quinoline-8-carboxylic acid (285 mg, 1.0 mmol), thiazol-2-amine (100 mg, 1.0 mmol), HATU (760 mg, 2.0 mmol) and DIPEA (258 mg, 2.0 mmol) in DMF (10 mL) was stirred at 50° C. for 10 hours. The mixture was cooled to room temperature and water (20 mL) was added. The mixture was extracted with ethyl acetate (3×25 mL), and the organic layer was dried over anhydrous Na2SO4, concentrated in vacuo and purified by chromatography on silica gel (5% Methanol in CH2Cl2) to give 2-(2-chloropyridin-4-yl)-N-(thiazol-2-yl)quinoline-8-carboxamide (290 mg, 79% yield).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe mixture was extracted with ethyl acetate (3×25 mL)
  3. dry with materialthe organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. custompurified by chromatography on silica gel (5% Methanol in CH2Cl2)

Sources & evidence

ORD record
ord-f79082c93cf4495cb8a4f27fb271ff8e
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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