Ethyl isocyanate → HCID 58452949, compound

HRID 1876833Notes

Reaction equation

HRID 1876833 reaction equation
[CH3:1][C@:2]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:11]2[C:6]3=[C:7]([C@:13]([CH3:22])([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:14][CH2:15][N:5]3[CH2:4][CH2:3]1)[CH:8]=[C:9]([NH2:12])[CH:10]=2.[CH2:29]([N:31]=[C:32]=[O:33])[CH3:30]>ClCCl>[CH3:1][C@:2]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:11]2[C:6]3=[C:7]([C@:13]([CH3:22])([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:14][CH2:15][N:5]3[CH2:4][CH2:3]1)[CH:8]=[C:9]([NH:12][C:32]([NH:31][CH2:29][CH3:30])=[O:33])[CH:10]=2

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 58452964HCID 58452964, compound

Product 1

HCID 58452949HCID 58452949, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution (1S,7S)-1,7-dimethyl-9-amino-1,7-diphenyl-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinoline (9), (110 mg, 0.30 mmol) in dichloromethane (15 mL) was added ethyl isocyanate (0.026 mL, 0.328 mmol), mmol) under argon at 0° C. The reaction mixture was then stirred at room temperature for overnight. The solvent was removed under reduced pressure and purified by MPLC) using silica gel column with 15 to 20% EtOAc:Hexane to get 1-((1S,7S)-1,7-dimethyl-1,7-diphenyl-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-yl)-3-ethylurea (249), (96 mg 73%). 1H NMR (300 MHz, Acetone-d6) δ ppm 1.00 (t, J=7.18 Hz, 3H) 1.71 (s, 6H) 1.91-2.02 (m, 2H) 2.15-2.31 (m, 2H) 2.75-2.87 (m, 2H) 2.90-3.03 (m, 2H) 3.03-3.16 (m, 2H) 6.98 (s, 2H) 7.09-7.31 (m, 10H)

Workup

  1. customThe solvent was removed under reduced pressure
  2. custompurified by MPLC)

Sources & evidence

ORD record
ord-3bbd53a5e98f4f1c9248c71bf531deed
Source dataset
uspto-grants-2012_11
Patent number
US08309729B2

Reaction notes

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