HCID 20523603, compound → HCID 13036383, compound

HRID 1156017Notes

Reaction equation

HRID 1156017 reaction equation
Cl.[N:2]1[C:6]2=[CH:7][CH:8]=[CH:9][CH:10]=[CH:11][C:5]2=[N:4][C:3]=1[N:12]1[CH2:17][CH2:16][N:15]([C:18]2[N:27]=[C:26]([NH2:28])[C:25]3[C:20](=[CH:21][C:22]([O:31][CH3:32])=[C:23]([O:29][CH3:30])[CH:24]=3)[N:19]=2)[CH2:14][CH2:13]1>CO.[Rh]>[NH:4]1[C:5]2[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:2]=[C:3]1[N:12]1[CH2:17][CH2:16][N:15]([C:18]2[N:27]=[C:26]([NH2:28])[C:25]3[C:20](=[CH:21][C:22]([O:31][CH3:32])=[C:23]([O:29][CH3:30])[CH:24]=3)[N:19]=2)[CH2:14][CH2:13]1

Participants

4

Reactant 1

HCID 20523603HCID 20523603, compound

Product 1

HCID 13036383HCID 13036383, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-[4-(2-cycloheptimidazolyl)-1-piperazinyl]-6,7-dimethoxy-4-quinazolinamine hydrochloride (1.0 g, described in Example 2) and 5% rhodium on carbon (0.10 g) in methanol (600 ml) was hydrogenated under an atmosphere of hydrogen at 50 lb/sq. in. pressure. The mixture was filtered and the filtrate was evaporated. The residue was dissolved in methanol and the solution was acidified with a few drops of 2 N hydrochloric acid. Acetone was added and crystals of the title compound were collected (0.880 g); mp>250° C.; ir (nujol) 3340 and 3160 cm-1 ; uv max (MeOH) 250 (ε=56500), 330 (ε=8200) and 342 nm (ε=7850); and nmr (DMSO-d6) δ 1.65 (m, 6H), 2.6 (m, 4H), 3.75 (m, 4H), 3.85 (s, 6H), 4.05 (m, 4H), 7.7 (s, 1H) and 7.75 (s, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in methanol
  4. additionAcetone was added
  5. customcrystals of the title compound were collected (0.880 g)

Sources & evidence

ORD record
ord-4de6b46839ef46f39d57896cd7b650b2
Source dataset
uspto-grants-1982_06
Patent number
US04333937

Reaction notes

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