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Methylamine → N-(2-(2,4-dimethylthiazol-5-yl)-3-methyl-4-oxo-3,4-dihydroquinazolin-8-yl)pyrazine-2-carboxamide

HRID 520449
Notes
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Reaction equation

HRID 520449 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:8]2O[C:10](=[O:27])[C:11]3[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][C:19]([C:21]4[CH:26]=[N:25][CH:24]=[CH:23][N:22]=4)=[O:20])[C:12]=3[N:13]=2)=[C:5]([CH3:7])[N:6]=1.[CH3:28][NH2:29]>CO>[CH3:1][C:2]1[S:3][C:4]([C:8]2[N:29]([CH3:28])[C:10](=[O:27])[C:11]3[C:12](=[C:14]([NH:18][C:19]([C:21]4[CH:26]=[N:25][CH:24]=[CH:23][N:22]=4)=[O:20])[CH:15]=[CH:16][CH:17]=3)[N:13]=2)=[C:5]([CH3:7])[N:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6329MethylamineHCID 58552812n-(2-(2,4-Dimethylthiazol-5-yl)-4-oxo-4h-benzo[d][1,3]oxazin-8-yl)pyrazine-2-carboxamide

Product 1

HCID 58552911N-(2-(2,4-dimethylthiazol-5-yl)-3-methyl-4-oxo-3,4-dihydroquinazolin-8-yl)pyrazine-2-carboxamideYield 31%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

N-(2-(2,4-dimethylthiazol-5-yl)-4-oxo-4H-benzo[d][1,3]oxazin-8-yl)pyrazine-2-carboxamide 18 (100 mg, 0.26 mmol) was dissolved in 30 wt % solution of CH3NH2 in methanol (10 mL). The reaction mixture was heated at 80° C. for 12 h. The resulting precipitate was collected by filtration and rinsed with DME to give Compound 287 (32 mg, 31% yield). MS (ESI) calc. for C19H16F3N6O2S: 392.11. found: 393 [M+H].

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washrinsed with DME

Sources & evidence

ORD record
ord-9d96df94117341cca194a9a2038d82a0
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09326986B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes