Dimethylformamide → HCID 54612772, compound

HRID 573373Notes

Reaction equation

HRID 573373 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=O.CN(C=O)C.C(N=C=NCCCN(C)C)C.[NH2:35][C:36]1[S:37][C:38]2[CH:44]=[C:43]([F:45])[CH:42]=[CH:41][C:39]=2[N:40]=1>>[F:45][C:43]1[CH:42]=[CH:41][C:39]2[N:40]=[C:36]([NH:35][C:12](=[O:14])[C:11]3[CH:15]=[CH:16][CH:17]=[N:18][C:10]=3[NH:9][C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[S:37][C:38]=2[CH:44]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 3199542-Amino-6-fluorobenzothiazoleHCID 1448057HCID 1448057, compound

Product 1

HCID 54612772HCID 54612772, compound

Conditions

Temperature
27 °C

Procedure

Compound 13 (185 mg, 1 mmol) and 2,4-dichloro aniline (18, 92 mg, 1 mmol) was taken in ethylene glycol and refluxed at 160° C. for 5 h. Then the reaction mixture was cooled and extracted in ethyl acetate (4×25 mL) from the aqueous layer and concentrated in vacuo. The compound was further purified by column chromatography using 60-120 silica gel (ethyl acetate/hexane, 1:9) to obtain Ethyl. 2-(2,4-dichloro anilino) nicotinate (25) as pure product. Ethyl 2-(2,4-dichloro anilino) nicotinate (25, 311 mg, 1 mmol) were refluxed with 2N NaOH in ethanol for 2 h. The reaction mixture was cooled and left acidified with 2N HCl white solids obtained, filtered and washed with water to give pure compound of 2-(2,4-dichlorophenylamino)nicotinic acid (32). To a stirred solution of 2-(2,4-dichlorophenylamino)nicotinic acid (32, 283 mg, 1 mmol) in dry DMF (10 mL) hydroxy benzotriazole HOBt (1.2 mmol) were added at 0° C. After 10 min 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDCI) (1.2 mmol) was added and finally 2-amino 6-fluoro benzothiazole (36, 117 mg, 0.7 mmol) were added Then the resulting mixture was stirred at room temperature (27° C.) for 8-10 h and then the reaction mixture was quenched with NaHCO3 and extracted in ethyl acetate (4×25 mL) from the ice cold aqueous layer and dried over anhydrous Na2SO4. The resulting product (10) was purified by column chromatography employing EtOAc/hexane as an eluent.

Workup

  1. customthe reaction mixture was quenched with NaHCO3
  2. extractionextracted in ethyl acetate (4×25 mL) from the ice cold aqueous layer
  3. dry with materialdried over anhydrous Na2SO4
  4. customThe resulting product (10) was purified by column chromatography

Sources & evidence

ORD record
ord-cfcf104d3c1742078930315c6c284db6
Source dataset
uspto-grants-2015_05
Patent number
US09029553B2

Reaction notes

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