Ammonia → HCID 178510960, compound

HRID 277170Notes

Reaction equation

HRID 277170 reaction equation
[Cl:1][C:2]1[CH:41]=[CH:40][C:5]([CH2:6][NH:7][S:8](/[CH:11]=[CH:12]/[CH2:13][CH2:14][CH2:15][C:16]2[N:17]=[CH:18][N:19](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:20]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(O)C.[NH3:45]>C1COCC1>[NH2:45][CH:12]([CH2:13][CH2:14][CH2:15][C:16]1[N:17]=[CH:18][NH:19][CH:20]=1)[CH2:11][S:8]([NH:7][CH2:6][C:5]1[CH:40]=[CH:41][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 702EthanolHCID 18314085HCID 18314085, compound

Product 1

HCID 178510960HCID 178510960, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of (E)-N-(4-chlorobenzyl)-5-(1-(triphenylmethyl)imidazol-4-yl)-1-pent-1-enesulfonamide (Example 5, step e) (290 mg, 0.50 mmol), ethanol saturated with ammonia (10 ml) and THF (10 ml) was sealed in a Teflon-lined pressure vessel and heated at 120° C. overnight. The solution was allowed to cool and the solvent evaporated. The residue was purified by flash column chromatography (silica, 1:10:90 ammonia(880)/methanol/dichloromethane) to give the title compound was obtained as a white solid (123 mg, 79%): 1H NMR (300 MHz, d6-DMSO) 7.92(1H, br s), 7.61(1H, d), 7.41(4H, m), 6.58(1H, d), 4.54(1H, m), 4.21(2H, s), 3.65(1H, dd), 3.50(1H, dd), 3.29(2H, s), 2.67(2H, m), 2.65(2H, t), 2.10(1H, m), 1.95(1H, m), 1.81(1H, m), 1.66(1H, m). Found: C, 50.17; H, 5.99; N, 15.48%; C15H21ClN4O2S requires: C, 50.48; H, 5.93; N, 15.70%.

Workup

  1. temperatureto cool
  2. customthe solvent evaporated
  3. customThe residue was purified by flash column chromatography (silica, 1:10:90 ammonia(880)/methanol/dichloromethane)

Sources & evidence

ORD record
ord-2ff59a34b2f347519b241fdc077057c7
Source dataset
uspto-grants-2002_03
Patent number
US06355665B1

Reaction notes

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