4-(2,4-Dimethoxyphenyl)butan-1-amine → HCID 178490100, compound

HRID 1296462Notes

Reaction equation

HRID 1296462 reaction equation
I.[NH2:2][C:3]1[C:4]([C:11]([NH:13][C:14](=[NH:17])SC)=[O:12])=[N:5][C:6]([Cl:10])=[C:7]([NH2:9])[N:8]=1.[CH3:18][O:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=1[CH2:28][CH2:29][CH2:30][CH2:31][NH2:32]>C1COCC1>[ClH:10].[CH3:18][O:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=1[CH2:28][CH2:29][CH2:30][CH2:31][NH:32][C:14]([NH:13][C:11]([C:4]1[C:3]([NH2:2])=[N:8][C:7]([NH2:9])=[C:6]([Cl:10])[N:5]=1)=[O:12])=[NH:17]

Participants

4

Reactant 2

HCID 225661354-(2,4-Dimethoxyphenyl)butan-1-amineHCID 140329753methyl N-(3,5-diamino-6-chloropyrazine-2-carbonyl)carbamimidothioate;hydroiodide

Product 1

HCID 178490100HCID 178490100, compoundYield 181.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(3,5-Diamino-6-chloropyrazinoyl-2-methyl-pseudothiourea hydroiodide (0.3 g, 0.77 mmol) was added to an anhydrous THF solution (30 mL) of 79 (0.4 g, 1.9 mmol). The reaction mixture was stirred at reflux for 3 h then the solvent was evaporated. The residue was washed with ethyl acetate (2×20 mL) then treated with 3% HCl (15 mL). The yellow solid that formed was separated, washed with water and dried overnight to provide compound 80 (0.32 g, 90%). 1H NMR (300 MHz, DMSO-d6) δ 1.57 (s, 4H), 2.50 (br s, 2H), 3.35 (br s, 2H), 3.73 (s, 3H), 3.76 (s, 3H), 6.43 (m, 1H), 6.52 (s, 1H), 7.02 (m, 1H), 7.45 (br s, 2H), 8.86 (br s, 1H), 8.99 (br s, 1H), 9.03 (m, 1H), 10.56 (s, 1H). APCI MS m/z 422 [C18H24ClN7O3+H]+.

Workup

  1. temperatureat reflux for 3 h
  2. customthe solvent was evaporated
  3. washThe residue was washed with ethyl acetate (2×20 mL)
  4. additionthen treated with 3% HCl (15 mL)
  5. customThe yellow solid that formed
  6. customwas separated
  7. washwashed with water
  8. customdried overnight

Sources & evidence

ORD record
ord-f9a64e8a1cb446dda49994da736cb513
Source dataset
uspto-grants-2007_07
Patent number
US07247636B2

Reaction notes

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