Hydrochloric Acid → HCID 178464162, compound

HRID 630086Notes

Reaction equation

HRID 630086 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:18](=[NH:24])[N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[CH:5]=[CH:6][C:7]=1[CH2:8][S:9][C:10]1[N:15]=[C:14]([OH:16])[CH:13]=[C:12]([CH3:17])[N:11]=1.[ClH:25].O1CCOCC1>CO>[ClH:1].[ClH:25].[Cl:1][C:2]1[CH:3]=[C:4]([C:18](=[NH:24])[N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[CH:5]=[CH:6][C:7]=1[CH2:8][S:9][C:10]1[N:15]=[C:14]([OH:16])[CH:13]=[C:12]([CH3:17])[N:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178464161HCID 178464161, compound

Product 1

HCID 178464162HCID 178464162, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-chloro-N,N-diethyl-4-{[(4-hydroxy-6-methylpyrimidin-2-yl)sulfanyl]methyl}benzene-1-carboximidamide (83 mg, 227 μmol) was stirred in methanol (10 mL), and a solution of 4 N HCl in dioxane (170 μL, 681 μmol) was added dropwise at 0° C. The mixture was stirred for 1.5 hours at room temperature. The solvent was removed by evaporation, and the residue was triturated with diethyl ether and dried in vacuo to afford to 3-chloro-N,N-diethyl-4-{[(4-hydroxy-6-methylpyrimidin-2-yl)sulfanyl]methyl}benzene-1-carboximidamide dihydrochloride (80 mg, 81% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.15 (t, J=7.2 Hz, 6H), 2.21 (s, 3H), 2.84-2.93 (m, 4H), 4.51 (s, 2H), 6.04 (bs, 1H), 7.51-7.54 (m, 1H), 7.81-7.84 (m, 2H); LRMS (ES+) m/z 365 (100%, M+1).

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was triturated with diethyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-19a5b3ff2c054dc1849dd86225d35489
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

Loading…