Ethanol → HCID 13036381, compound

HRID 1703173Notes

Reaction equation

HRID 1703173 reaction equation
[Na].Cl[C:3]1[CH:4]=[CH:5][C:6]2[C:7](=[CH:32][CH:33]=1)[N:8]=[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]3[N:26]=[C:25]([NH2:27])[C:24]4[C:19](=[CH:20][C:21]([O:30][CH3:31])=[C:22]([O:28][CH3:29])[CH:23]=4)[N:18]=3)[CH2:13][CH2:12]1)[N:10]=2.O.[CH2:35]([OH:37])[CH3:36]>>[CH2:35]([O:37][C:3]1[CH:4]=[CH:5][C:6]2[C:7](=[CH:32][CH:33]=1)[N:8]=[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]3[N:26]=[C:25]([NH2:27])[C:24]4[C:19](=[CH:20][C:21]([O:30][CH3:31])=[C:22]([O:28][CH3:29])[CH:23]=4)[N:18]=3)[CH2:13][CH2:12]1)[N:10]=2)[CH3:36]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 5360545SodiumHCID 13036375HCID 13036375, compound

Product 1

HCID 13036381HCID 13036381, compound

Procedure

A solution of sodium (0.53 g) in ethanol (22 ml) was added over a period of 1 hr to a suspension of 2-[4-(6-chloro-2-cycloheptimidazolyl)-1-piperazinyl]-6,7-dimethoxy-4-quinazolinamine (2.6 g, described in Example 2). The resulting mixture was stirred at 20°-25° C. for 2 hr, refluxed for 1 hr, cooled and poured into water at 0° to 5° C. The precipitate was collected, washed with water, dried and chromatographed through silica gel using methanoldichloromethane (1:9). The eluates were evaporated to give the title compound (1.18 g): mp>250° C.; ir (nujol) 3430, 3300 and 3170 cm-1 ; uv max (MeOH) 214 (ε=27685), 253 (ε=70380), 275 (ε=38560), 370 (ε=38560) and 390 nm (ε=21950); nmr (DMSO-d6) δ 1.4 (t, 3H), 3.9 (m, 14H), 6.75 (s, 1H), 7.17 (s, 2H), 7.4 (s, 1H), and 7.5-8 (m, 4H); and Anal. Calcd for C24H27N7O3 : C, 62.46% H, 5.90% N, 21.24% and Found: C, 62.13% H, 6.01% N, 20.95%.

Workup

  1. temperaturerefluxed for 1 hr
  2. temperaturecooled
  3. customThe precipitate was collected
  4. washwashed with water
  5. customdried
  6. customchromatographed through silica gel using methanoldichloromethane (1:9)
  7. customThe eluates were evaporated

Sources & evidence

ORD record
ord-6fb752a4c51b4b948bec22c40de19bb6
Source dataset
uspto-grants-1982_09
Patent number
US04351832

Reaction notes

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