Putrescine → HCID 178512615, compound

HRID 66581Notes

Reaction equation

HRID 66581 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH:10]2[CH2:15][CH2:14][CH2:13][CH:12]([NH:16][C:17]3[C:20](=[O:21])[C:19](=[O:22])[C:18]=3OC)[CH2:11]2)[N:9]=1)[C:2]([NH2:4])=[NH:3].[CH3:25][OH:26].C(Cl)(Cl)Cl.[NH2:31][CH2:32][CH2:33][CH2:34][CH2:35][NH2:36]>CO>[NH:1]([C:5]1[S:6][CH:7]=[C:32]([CH:33]2[CH2:13][CH2:14][CH2:15][CH:35]([NH:36][C:18]3[C:25](=[O:26])[C:20](=[O:21])[C:17]=3[NH:16][CH2:12][CH2:11][CH2:10][CH2:8][NH:9][C:18]3[C:19](=[O:22])[C:20](=[O:21])[C:17]=3[NH:16][CH:12]3[CH2:13][CH2:14][CH2:15][CH:10]([C:8]4[N:9]=[C:5]([NH:1][C:2]([NH2:4])=[NH:3])[S:6][CH:7]=4)[CH2:11]3)[CH2:34]2)[N:31]=1)[C:2]([NH2:4])=[NH:3]

Participants

5

Reactant 3

HCID 1045PutrescineHCID 21584188Chloroform methanolHCID 178493670HCID 178493670, compound

Product 1

HCID 178512615HCID 178512615, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[3-(2-guanidinothiazol-4-yl)-cyclohexylamino]-2-methoxycyclobutene-3,4-dione (0.35 g.) in 60 ml. of methanol/chloroform (50:50 v/v) was added 1,4-diaminobutane (0.044 g.) in methanol (1 ml.). The solution was heated under reflux for 16 hours during which time a precipitate formed. The reaction mixture was cooled and the solid precipitate collected and washed with methanol (1 ml.) and ether (2 ml.) to give, as an off-white powder, 1,4-bis{1-[3-(2-guanidinothiazol-4-yl)cyclohexylamino]-3,4-dioxocyclobutenylamino}butane. The carbon-13 magnetic resonance spectrum (δ relative to tetramethylsilane) in d6 -DMSO included one carbon singlets at 182.3, 174.8, 167.7, 167.0, 156.7, 155.3, 100.3 and 52.4 together with a series of singlets from 42.9 to 24.0 p.p.m. (the latter group of signals includes the resonances due to the solvent).

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 16 hours during which time a precipitate
  3. customformed
  4. temperatureThe reaction mixture was cooled
  5. customthe solid precipitate collected
  6. washwashed with methanol (1 ml.) and ether (2 ml.)

Sources & evidence

ORD record
ord-0263457af80e450a9fa8b828f0f63347
Source dataset
uspto-grants-1982_08
Patent number
US04342765

Reaction notes

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