2-Methoxyaniline → HCID 54596226, compound

HRID 1853145Notes

Reaction equation

HRID 1853145 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:13][C:14]1[C:15]([C:27]([OH:29])=O)=[N:16][C:17]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:18][N:19]=1.[CH3:30][O:31][C:32]1[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=1[NH2:34]>CN(C=O)C>[NH2:13][C:14]1[C:15]([C:27]([NH:34][C:33]2[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=2[O:31][CH3:30])=[O:29])=[N:16][C:17]([NH:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[CH:18][N:19]=1

Participants

5

Reactant 3

HCID 70002-MethoxyanilineHCID 682631,1'-CarbonyldiimidazoleHCID 58084306HCID 58084306, compound

Product 1

HCID 54596226HCID 54596226, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

CDI (92.98 mg, 0.5734 mmol) was added to a solution of 3-amino-6-anilino-pyrazine-2-carboxylic acid (110 mg, 0.4778 mmol) in DMF (1.5 mL) and the reaction stirred at ambient temperature for 1 hour. 2-Methoxyaniline (88.26 mg, 0.7167 mmol) was added and the reaction mixture left to stir at ambient temperature for 48 hours. The reaction mixture was purified directly by reverse phase preparative HPLC [Waters Sunfire C18, 10 mM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected, passed through a sodium bicarbonate cartridge and freeze-dried to give the title compound as an orange solid (14 mg, 9% Yield). 1H NMR (400.0 MHz, DMSO) δ 3.84 (s, 3H), 6.90-7.10 (m, 6H), 7.29-7.33 (m, 2H), 7.53-7.55 (m, 2H), 8.13 (s, 1H), 8.41-8.43 (m, 1H), 9.18 (s, 1H) and 10.15 (s, 1H) ppm; MS (ES+) 336.07.

Workup

  1. waitthe reaction mixture left
  2. stirringto stir at ambient temperature for 48 hours
  3. customThe reaction mixture was purified directly by reverse phase preparative HPLC [Waters Sunfire C18, 10 mM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]
  4. customThe fractions were collected
  5. customfreeze-dried

Sources & evidence

ORD record
ord-acb192c146644172bdf2aecc29d189e8
Source dataset
uspto-grants-2015_02
Patent number
US08962631B2

Reaction notes

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