Pyrrolidine → HCID 10570627, compound

HRID 1736708Notes

Reaction equation

HRID 1736708 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:21]=[CH:22][N:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[NH:26][CH2:25][C:24]=23)=[CH:16][CH:15]=1.[CH:33]([N:36]([CH:39]([CH3:41])C)CC)([CH3:35])C.N1CCCC1>C(Cl)Cl>[F:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[N:21]=[CH:22][N:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]([C:5]([N:36]4[CH2:33][CH2:35][CH2:41][CH2:39]4)=[O:11])[CH2:25][C:24]=23)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 10659340HCID 10659340, compound

Product 1

HCID 10570627HCID 10570627, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphosgene (427 mg) is added to a mixture of 3-(4-fluorophenyl)-4,5-dihydroimidazo[1,5-a]quinoxaline (XXXVI, EXAMPLE 247, 702 mg), methylene chloride (27.0 ml) and diisopropylethylamine (0.53 ml) at 0°. The resultant solution is stirred for 1 hr at 0° and for 2 hr at 20°-25°. The mixture is cooled to 0° and pyrrolidine (0.85 ml) is added. The mixture is maintained at 0° for 1 hr and is allowed to warm to 20°-25°. After stirring for 16 basic workup using sodium bicarbonate, methylene chloride and magnesium sulfate and purification by flash chromatography eluting with ethyl acetate/hexane (1/1), pooling the appropriate fractions and concentration gives the product. Recrystallization from hot ethyl acetate-hexane give the title compound, mp 217°-218°; IR (mineral oil) 2925, 1641, 1506, 1414 and 753 cm-1 ; NMR (CDCl3) 8.07, 7.64, 7.53, 7.05-7.3, 4.89, 3.25 and 1.7-1.85 δ; MS (m/z) 362, 264, 98 and 55.

Workup

  1. temperatureThe mixture is cooled to 0°
  2. temperatureThe mixture is maintained at 0° for 1 hr
  3. temperatureto warm to 20°-25°
  4. customsodium bicarbonate, methylene chloride and magnesium sulfate and purification by flash chromatography
  5. washeluting with ethyl acetate/hexane (1/1)
  6. concentrationthe appropriate fractions and concentration
  7. customgives the product
  8. customRecrystallization from hot ethyl acetate-hexane

Sources & evidence

ORD record
ord-55447e9abb194ed894b8680951c35fd9
Source dataset
uspto-grants-1996_07
Patent number
US05541324

Reaction notes

Loading…