HCID 22402750, compound → HCID 22402747, compound

HRID 260173Notes

Reaction equation

HRID 260173 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]([NH:11][C:12](=[N:20][C:21]#[N:22])OC2C=CC=CC=2)[CH:7]=[C:8]([I:10])[CH:9]=1)=[N+:2]=[N-:3].[F:23][C:24]1[CH:25]=[C:26]([C:30]2([NH2:34])[CH2:33][CH2:32][CH2:31]2)[CH:27]=[CH:28][CH:29]=1>C(O)(C)C>[N:1]([C:4]1[CH:5]=[C:6]([NH:11][C:12]([NH:20][C:21]#[N:22])=[N:34][C:30]2([C:26]3[CH:27]=[CH:28][CH:29]=[C:24]([F:23])[CH:25]=3)[CH2:33][CH2:32][CH2:31]2)[CH:7]=[C:8]([I:10])[CH:9]=1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 22402750HCID 22402750, compoundHCID 178512287HCID 178512287, compound

Product 1

HCID 22402747HCID 22402747, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
82 °C

Procedure

Step B-2. To a stirred suspension of N-(3-azido-5-iodophenyl)-N'-cyanocarbamimidic acid, phenyl ester (B-1, 472 mg 1.16 mmol) in isopropanol was added 1-(3-fluorophenyl)cyclobutanamine (227 mg, 1.40 mmol). The reaction mixture was heated in a sealed tube at 82° C. overnight. The cooled reaction mixture was concentrated. The residue was purified by medium pressure liquid chromatography using 30% ethyl acetate in hexane as the eluent to afford 0.257 g of N-(3-azido-5-iodophenyl)-N'-cyano-N"-[1-(3-fluorophenyl)cyclobutyl]guanidine. (B-2). Mp=171°-173° C. (dec). IR (mull) 3195, 3135, 3078, 3002, 2953, 2925, 2854, 2188, 2110, 1614, 1608, 1587, 1573, 1542, 1448, 1440, 1430, 1365, 1309, 1292, 1245, 1221, 1162, 1041, 874 cm-1 ; 1H NMR (CDCl3) δ7.42 (m, 1 H), 7.26 (m, 2 H), 7.17 (m, 2 H), 7.06 (m, 1 H), 6.78 (m, 1 H), 2.59 (m, 4 H), 2.15 (m, 1 H), 2.00 (m, 1 H), 1.61 2, 2 H); 13C NMR (CDCl3) δ156.4, 138.0, 131.3, 124.9, 120.6, 116.3, 114.7, 114.4, 112.8, 112.5, 94.9, 59.6, 34.7, 14.8; Mass Spec (FAB) m/z 476 (M+1), 448, 434, 421, 350, 328, 300, 273, 216, 173, 149 (base). Exact mass calculated for C18H16FIN7 : 476.0498. Found: 476.0514. Analysis calculated for C18H15FIN7 : C, 45.49; H, 3.18; N, 20.63. Found: C, 45.23; H, 3.16; N, 20.37.

Workup

  1. customThe cooled reaction mixture
  2. concentrationwas concentrated
  3. customThe residue was purified by medium pressure liquid chromatography

Sources & evidence

ORD record
ord-d9b138cf9a2a4feab8ca554154e2f871
Source dataset
uspto-grants-1996_06
Patent number
US05525742

Reaction notes

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