Dimethylformamide → HCID 54765287, compound

HRID 573371Notes

Reaction equation

HRID 573371 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:19]=[CH:18][CH:17]=[CH:16][C:12]=2[C:13]([OH:15])=O)[CH:5]=[C:6]([F:9])[C:7]=1[F:8].CN(C=O)C.C(N=C=NCCCN(C)C)C.[NH2:36][C:37]1[S:38][C:39]2[CH:45]=[C:44]([N+:46]([O-:48])=[O:47])[CH:43]=[CH:42][C:40]=2[N:41]=1>>[N+:46]([C:44]1[CH:43]=[CH:42][C:40]2[N:41]=[C:37]([NH:36][C:13]([C:12]3[C:11]([NH:10][C:4]4[CH:5]=[C:6]([F:9])[C:7]([F:8])=[C:2]([F:1])[CH:3]=4)=[N:19][CH:18]=[CH:17][CH:16]=3)=[O:15])[S:38][C:39]=2[CH:45]=1)([O-:48])=[O:47]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 227042-Amino-6-nitrobenzothiazoleHCID 62814075HCID 62814075, compound

Product 1

HCID 54765287HCID 54765287, compound

Conditions

Temperature
27 °C

Procedure

Compound 13 (185 mg, 1 mmol) and 3,4,5-trifluoro aniline (19, 147 mg, 1 mmol) was taken in ethylene glycol and refluxed at 150° 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-(3,4,5 trifluoroanilino) nicotinate (26) as pure product. Ethyl 2-(3,4,5 trifluoroanilino) nicotinate (26, 296 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-(3,4,5-trifluorophenylamino) nicotinic acid (33). To a stirred solution of 2-(3,4,5-trifluorophenylamino) nicotinic acid (33, 252 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-nitro benzothiazole (37, 137 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 (8) 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 (8) was purified by column chromatography

Sources & evidence

ORD record
ord-2971f342c5474563b78596285318a2eb
Source dataset
uspto-grants-2015_05
Patent number
US09029553B2

Reaction notes

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