Hydrochloric Acid → HCID 44229381, compound

HRID 1951306Notes

Reaction equation

HRID 1951306 reaction equation
Cl.[O:2]=[C:3]1[N:12]([CH2:13][CH2:14][CH2:15][N:16]([CH2:20][CH2:21][CH2:22][CH2:23][NH:24][CH2:25][CH2:26][CH2:27][N:28]2[C:37](=[O:38])[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[NH:30][C:29]2=[O:39])[C:17](=[O:19])[CH3:18])[C:11](=[O:40])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4]1.[CH2:41](N(CC)CC)C.C=O.[BH4-].[Na+]>ClCCl.CO>[O:2]=[C:3]1[N:12]([CH2:13][CH2:14][CH2:15][N:16]([CH2:20][CH2:21][CH2:22][CH2:23][N:24]([CH2:25][CH2:26][CH2:27][N:28]2[C:37](=[O:38])[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[NH:30][C:29]2=[O:39])[CH3:41])[C:17](=[O:19])[CH3:18])[C:11](=[O:40])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 442293781176758-04-5

Product 1

HCID 44229381HCID 44229381, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Hydrochloride acid salt of N-[3-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)propyl]-N-{4-[3-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)propylamino]butyl}acetamide (2 g, 3.5 mmol was dissolved in 80 mL dichloromethane and 10 mL, methanol. Triethylamine (0.45 g, 4.5 mmol) and paraformaldehyde (0.14 g, 4.5 mmol) was added thereto and stirred for 2 hours at room temperature. After concentration of the solvent, 40 mL methanol and sodium borohydride (0.76 g, 20.2 mmol) were added thereto and stirred for 15 hours. After removal of methanol by distillation under reduced pressure, silica gel column-chromatography of the remaining residue was performed to give the title compound of white solid (1.2 g, 62%).

Workup

  1. stirringstirred for 15 hours
  2. customAfter removal of methanol
  3. distillationby distillation under reduced pressure, silica gel column-chromatography of the remaining residue

Sources & evidence

ORD record
ord-3cd90ad7aae74a18947ca02117a2e167
Source dataset
uspto-grants-2013_03
Patent number
US08404696B2

Reaction notes

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