Aminopyrazine → HCID 54695959, compound

HRID 1730545Notes

Reaction equation

HRID 1730545 reaction equation
CO[C:3]([C:5]1[N:6]([CH3:22])[S:7](=[O:21])(=[O:20])[C:8]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][C:9]=2[C:10]=1[OH:11])=[O:4].[NH2:23][C:24]1[CH:29]=[N:28][CH:27]=[CH:26][N:25]=1>C1(C)C(C)=CC=CC=1>[OH:11][C:10]1[C:9]2[CH:12]=[CH:13][C:14]3[C:19]([C:8]=2[S:7](=[O:20])(=[O:21])[N:6]([CH3:22])[C:5]=1[C:3]([NH:23][C:24]1[CH:29]=[N:28][CH:27]=[CH:26][N:25]=1)=[O:4])=[CH:18][CH:17]=[CH:16][CH:15]=3

Participants

4

Reactant 2

HCID 78747Aminopyrazine2×HCID 546906514-hydroxy-2-methyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxylic acid methylester-1,1-dioxide

Product 1

HCID 54695959HCID 54695959, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture consisting of 4.8 gm (0.015 mol) of 4-hydroxy-2-methyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxylic acid methylester-1,1-dioxide, 2.1 gm (0.022 mol) of aminopyrazine and 200 ml of dry xylene was refluxed for 8 hours in a Soxhlet apparatus equipped with 4-A-molecular sieve. Then, another 0.5 gm of aminopyrazine was added, the mixture was refluxed for 8 hours more, and then allowed to cool and stand overnight. The precipitate formed thereby was suctionfiltered off, and thefiltrate was evaporated in vacuo. The combined precipitate and evaporation residue was recyrstallized from ethyl acetate, yielding 3.0 gm (52% of theory) of 4-hydroxy-2-methyl-N-pyrazinyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1dioxide, m.p. 245° C (decomp.).

Workup

  1. temperaturewas refluxed for 8 hours in a Soxhlet apparatus
  2. customequipped with 4-A-molecular sieve
  3. temperaturethe mixture was refluxed for 8 hours more
  4. temperatureto cool
  5. customThe precipitate formed
  6. customthefiltrate was evaporated in vacuo
  7. customThe combined precipitate and evaporation residue

Sources & evidence

ORD record
ord-be80b9136bc941d1a2dfd426ebb150d9
Source dataset
uspto-grants-1976_11
Patent number
US03992535

Reaction notes

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