Methanol → HCID 178449225, compound

HRID 25142Notes

Reaction equation

HRID 25142 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.OCCOC1C=CC([CH2:28][CH2:29][CH2:30][CH2:31][NH2:32])=CC=1.CO.C(N(C(C)C)CC)(C)C>C1COCC1>[ClH:10].[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])[CH2:30][CH2:29][CH3:28]

Participants

6

Reactant 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 11537093HCID 11537093, compoundHCID 140329753methyl N-(3,5-diamino-6-chloropyrazine-2-carbonyl)carbamimidothioate;hydroiodide

Product 1

HCID 178449225HCID 178449225, compoundYield 194%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(3,5-Diamino-6-chloropyrazinoyl-2-methyl-pseudothiourea hydroiodide (0.32 g, 0.8 mmol) was added to a solution of amine 115 (0.25 g, 1.2 mmol) in a mixture of THF (15 mL), methanol (5 mL) and diisopropylethylamine (1 mL). The reaction mixture was stirred at reflux for 3.5 h and then cooled to room temperature. The formed precipitate was isolated, washed with ethyl acetate (2×5 mL) and treated with 5% HCl (10 mL). The resulting solid was isolated by filtration, washed with water and dried under vacuum to give compound 116 (0.25 g, 73%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 1.56 (m, 4H), 2.57 (m, 2H), 3.32 (m, 2H), 3.70 (m, 2H), 3.93 (m, 2H), 4.90 (t, 1H), 6.84 (d, 2H), 7.12 (d, 2H), 7.45 (s, 2H), 8.70 (br s, 1H), 8.88 (br s, 1H), 9.12 (br s, 1H) 10.45 (s, 1H). APCI MS m/z=422 [C18H24ClN7O3+H]+.

Workup

  1. temperatureat reflux for 3.5 h
  2. customThe formed precipitate was isolated
  3. washwashed with ethyl acetate (2×5 mL)
  4. additiontreated with 5% HCl (10 mL)
  5. customThe resulting solid was isolated by filtration
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-c0a070977d2c451284950da28aab1df3
Source dataset
uspto-grants-2005_02
Patent number
US06858615B2

Reaction notes

Loading…