Diethylamine → HCID 9924451, compound

HRID 1368059Notes

Reaction equation

HRID 1368059 reaction equation
Cl[CH2:2][C:3]([C:5]1[N:6]([CH3:22])[CH:7]=[C:8]([C:10]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)=[O:11])[CH:9]=1)=[O:4].[CH2:23]([NH:25][CH2:26][CH3:27])[CH3:24]>CCO>[CH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[CH:21][C:12]=1[C:10]([C:8]1[CH:9]=[C:5]([C:3](=[O:4])[CH2:2][N:25]([CH2:26][CH3:27])[CH2:23][CH3:24])[N:6]([CH3:22])[CH:7]=1)=[O:11]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 18519866HCID 18519866, compound

Product 1

HCID 9924451HCID 9924451, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2.5 g (0.008 mole) of 2-chloro-1-[4(2-naphthalenoyl)-1-methyl-1H-pyrrol-2-yl]ethanone and 2.5 mL (0.024 mole) of diethylamine was refluxed for 3 hr in 50 mL of EtOH. After cooling, the solvent was evaporated in vacuo. The residue was chromatographed on silica gel (90:10:1 CH2Cl2:MeOH:NH4OH). The resulting oil was treated with ethereal HCl in EtOH. The resulting gum was converted to the free base by partitioning between Et2O/NaHCO3. This was again chromatographed on silica gel (90:10:1 CH2Cl2:MeOH:NH4OH). The resulting oil was converted to the fumarate salt in 2-PrOH/EtOH. The solid was filtered to give 0.76 g (27%) of Compound 1. mp 130-132° C. CIMS m/z=349 (MH+). 1H NMR (300 MHz, CDCl3) δ 8.4 (Ar, 1H); 8.15-8.0 (Ar, 4H); 7.85 (Ar, 1H); 7.7-7.6 (Ar, 2H); 7.2 (Ar, 1H); 6.6 (s, 2H); 4.0 (s, 3H); 3.7 (s, 2H); 2.6 (q, 4H); 1.0 (t, 6H). Anal calc'd for: C22H24N2O2.C4H4O40.33H2O: C, 66.40; H, 6.14; N, 5.96. Found: C, 66.38; H, 6.43; N, 5.73, KF water 1.22.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was evaporated in vacuo
  3. customThe residue was chromatographed on silica gel (90:10:1 CH2Cl2:MeOH:NH4OH)
  4. additionThe resulting oil was treated with ethereal HCl in EtOH
  5. customby partitioning between Et2O/NaHCO3
  6. customThis was again chromatographed on silica gel (90:10:1 CH2Cl2:MeOH:NH4OH)
  7. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-315fbcaea7174c538f64467d60cf64b5
Source dataset
uspto-grants-2003_06
Patent number
US06573267B2

Reaction notes

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