Anthranilamide → N-[2-(Aminocarbonyl)phenyl]-2-(3-pyridinyl)-4-thiazolecarboxamide

HRID 1685484Notes

Reaction equation

HRID 1685484 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:8][CH:9]=[C:10]([C:12]([OH:14])=O)[N:11]=2)[CH:2]=1.[NH2:15][C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18]([NH2:20])=[O:19].O.ON1C2C=CC=CC=2N=N1.C1(N=C=NCCN2CCOCC2)CCCCC1>N1C=CC=CC=1.C(Cl)(Cl)Cl>[NH2:20][C:18]([C:17]1[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=1[NH:15][C:12]([C:10]1[N:11]=[C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[S:8][CH:9]=1)=[O:14])=[O:19]

Participants

7

Reactant 4

HCID 6942AnthranilamideHCID 849981-Cyclohexyl-3-(2-morpholinoethyl)carbodiimideHCID 7365132-(3-Pyridyl)thiazole-4-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 42639093N-[2-(Aminocarbonyl)phenyl]-2-(3-pyridinyl)-4-thiazolecarboxamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

2-(3-Pyridyl)thiazole-4-carboxylic acid (206 mg, 1 mmol) and 2-amino-benzamide (163 mg, 1.2 mmol) are mixed, and chloroform (10 ml) and pyridine (1.2 ml) are added. Then 1-hydroxybenzotriazole hydrate (230 mg) and 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-P-toluene-sulphonate CAS[2491-17-0] (635 mg) are added, and the mixture is stirred at room temperature for 20 h. The solid is filtered off with suction and washed with ethyl acetate, water and again with ethyl acetate. Purification of the solid by preparative HPLC results in Example 1.1 as a white foam (58 mg).

Workup

  1. filtrationThe solid is filtered off with suction
  2. washwashed with ethyl acetate, water and again with ethyl acetate
  3. customPurification of the solid by preparative HPLC

Sources & evidence

ORD record
ord-26f1893c3a47465ab21f7a7f4ab2eb7c
Source dataset
uspto-grants-2012_04
Patent number
US08148411B2

Reaction notes

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