Water → n-(2-(2,4-Dimethylthiazol-5-yl)-4-oxo-4h-benzo[d][1,3]oxazin-8-yl)pyrazine-2-carboxamide

HRID 520448Notes

Reaction equation

HRID 520448 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:8](Cl)=[O:9])=[C:5]([CH3:7])[N:6]=1.[NH2:11][C:12]1[C:20]([NH:21][C:22]([C:24]2[CH:29]=[N:28][CH:27]=[CH:26][N:25]=2)=[O:23])=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](O)=[O:15].O>N1C=CC=CC=1>[CH3:1][C:2]1[S:3][C:4]([C:8]2[O:9][C:14](=[O:15])[C:13]3[CH:17]=[CH:18][CH:19]=[C:20]([NH:21][C:22]([C:24]4[CH:29]=[N:28][CH:27]=[CH:26][N:25]=4)=[O:23])[C:12]=3[N:11]=2)=[C:5]([CH3:7])[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 146531402,4-Dimethylthiazole-5-carbonyl chlorideHCID 585528702-Amino-3-(pyrazine-2-carboxamido)benzoic acid

Product 1

HCID 58552812n-(2-(2,4-Dimethylthiazol-5-yl)-4-oxo-4h-benzo[d][1,3]oxazin-8-yl)pyrazine-2-carboxamideYield 81%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2,4-dimethylthiazole-5-carbonyl chloride 17 (104 mg, 0.58 mmol) was added to a suspension of 2-amino-3-(pyrazine-2-carboxamido)benzoic acid 16 (100 mg, 0.39 mmol) in pyridine (5 mL). The reaction mixture was stirred at room temperature for 12 h then poured into ice cooled H2O (30 mL). The resulting precipitate was collected by filtration, rinsed with H2O, and dried under vacuum to give 18 (110 mg, 81% yield).

Workup

  1. additionthen poured into ice
  2. filtrationThe resulting precipitate was collected by filtration
  3. washrinsed with H2O
  4. customdried under vacuum

Sources & evidence

ORD record
ord-a9a2563c3a2147cf88f850c7b4a59519
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

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