Hydrochloric Acid → HCID 10052335, compound

HRID 736612Notes

Reaction equation

HRID 736612 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].[NH2:10][C:11]1[C:12]([C:33](O)=[O:34])=[N:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([N:26]3[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]3)(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[CH:15][N:16]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C.[ClH:78]>CN(C)C=O.C(Cl)Cl.C(OCC)C>[ClH:78].[NH2:10][C:11]1[C:12]([C:33]([NH:5][C:4]2[CH:6]=[CH:7][CH:8]=[CH:9][C:3]=2[O:2][CH3:1])=[O:34])=[N:13][C:14]([C:17]2[CH:18]=[CH:19][C:20]([S:23]([N:26]3[CH2:27][CH2:28][N:29]([CH3:32])[CH2:30][CH2:31]3)(=[O:25])=[O:24])=[CH:21][CH:22]=2)=[CH:15][N:16]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 70002-MethoxyanilineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27960291-Hydroxybenzotriazole hydrateHCID 685325113-Amino-6-[4-[(4-methyl-1-piperazinyl)sulfonyl]phenyl]-2-pyrazinecarboxylic acid

Product 1

HCID 10052335HCID 10052335, compoundYield 12%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

2-Methoxyaniline (80 mg, 318 mmol) was added to a mixture of 3-amino-6-[4-[(4-methyl-1-piperazinyl)sulfonyl]phenyl]-2-pyrazinecarboxylic acid (80 mg, 212 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (82 mg, 255 mmol), 1-hydroxybenzotriazole hydrate (34 mg, 255 mmol) and N-ethyl-N,N-diisopropylamine (0.111 mL, 0.637 mmol) in N,N-dimethylformamide (2 mL). The reaction mixture was stirred for 13 h. The reaction was quenched with water (1 mL) and the solvent was evaporated. Purification by preparative HPLC (column: XTerra C8 19×300 mm, eluent: a acetonitrile/water, (20:80 to 80:20), gradient) followed by evaporation of the solvent gave a yellowish solid that was dissolved in methylene chloride (10 mL). HCl in diethyl ether (1 M, 2.5 mL) was added while stirring. Filtration and drying gave 12 mg (12% yield) of the title compound: MS (ESI) 483 m/z (M++1).

Workup

  1. customThe reaction was quenched with water (1 mL)
  2. customthe solvent was evaporated
  3. customPurification by preparative HPLC (column
  4. customXTerra C8 19×300 mm, eluent: a acetonitrile/water, (20:80 to 80:20), gradient) followed by evaporation of the solvent
  5. customgave a yellowish solid
  6. stirringwhile stirring
  7. filtrationFiltration
  8. customdrying

Sources & evidence

ORD record
ord-b6644d776fc842a1b45dc673f5e81984
Source dataset
uspto-grants-2009_09
Patent number
US07595319B2

Reaction notes

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