Anthranilamide → HCID 57737846, compound

HRID 598422Notes

Reaction equation

HRID 598422 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([OH:9])=O)[N:6]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:34][C:35]1[CH:43]=[CH:42][CH:41]=[CH:40][C:36]=1[C:37]([NH2:39])=[O:38].C(N(CC)C(C)C)(C)C>CN(C)C=O>[NH2:39][C:37]([C:36]1[CH:40]=[CH:41][CH:42]=[CH:43][C:35]=1[NH:34][C:7]([C:5]1[N:6]=[C:2]([Br:1])[S:3][CH:4]=1)=[O:9])=[O:38]

Participants

6

Reactant 4

HCID 6942AnthranilamideHCID 81531DiisopropylethylamineHCID 27632092-Bromo-1,3-thiazole-4-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 57737846HCID 57737846, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromo-4-thiazolecarboxylic acid (1 g), HATU (2.01 g) and 2-aminobenzamide (0.65 g) are introduced into N,N-dimethylformamide (DMF) (20 ml). The mixture is cooled with an ice bath, and N,N-diisopropylethylamine (0.90 ml) is added. The reaction mixture is stirred at room temperature for 6 days, poured into ice-water and allowed to thaw with stirring, and the precipitated solid is filtered off with suction, washed twice with water, twice with diethyl ether and dried in vacuo. Intermediate III.2 is obtained as a solid (1.4 g).

Workup

  1. temperatureThe mixture is cooled with an ice bath
  2. stirringwith stirring
  3. filtrationthe precipitated solid is filtered off with suction
  4. washwashed twice with water, twice with diethyl ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-77731f6d97124e189f08fdc3451fd289
Source dataset
uspto-grants-2011_03
Patent number
US07897626B2

Reaction notes

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