Triethylamine → HCID 178460090, compound

HRID 2374491Notes

Reaction equation

HRID 2374491 reaction equation
[NH2:1][C:2]1[C:3]([C:7]2[NH:23][C:10]3=[CH:11][C:12]4[C:13]([CH3:22])([CH3:21])[C:14](=[O:20])[N:15]([CH2:18][CH3:19])[C:16]=4[CH:17]=[C:9]3[N:8]=2)=[N:4][NH:5][CH:6]=1.C(N(CC)CC)C.[C:31](Cl)(=[O:34])[CH2:32][CH3:33]>ClCCl>[CH2:18]([N:15]1[C:16]2[CH:17]=[C:9]3[N:8]=[C:7]([C:3]4[C:2]([NH:1][C:31](=[O:34])[CH2:32][CH3:33])=[CH:6][NH:5][N:4]=4)[NH:23][C:10]3=[CH:11][C:12]=2[C:13]([CH3:22])([CH3:21])[C:14]1=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 178462936HCID 178462936, compound

Product 1

HCID 178460090HCID 178460090, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-amino-1H-pyrazol-3-yl)-5-ethyl-7,7-dimethyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one (150 mg, 0.48 mmol), triethylamine (0.20 ml, 14.50 mmol) in dichloromethane (8.0 ml), propionyl chloride (134 mg, 1.45 mmol) was added at room temperature. The mixture was stirred for 15 hours. The solvent was removed under diminished pressure. After evaporation, the mixture was stirred in acetonitrile/methanol (1:2, 9.0 ml) with aqueous ammonia (3.0 ml) for 3 hours. Water (50 ml) was added and the mixture was extracted three times with ethyl acetate (3×50 ml). The combined organic layers were washed with aqueous hydrochloric acid (1N), brine, dried and evaporated to afford a residue purified by HPLC. The title compound was obtained as white powder (19 mg).

Workup

  1. customThe solvent was removed under diminished pressure
  2. customAfter evaporation
  3. stirringthe mixture was stirred in acetonitrile/methanol (1:2, 9.0 ml) with aqueous ammonia (3.0 ml) for 3 hours
  4. additionWater (50 ml) was added
  5. extractionthe mixture was extracted three times with ethyl acetate (3×50 ml)
  6. washThe combined organic layers were washed with aqueous hydrochloric acid (1N), brine
  7. customdried
  8. customevaporated
  9. customto afford a residue
  10. custompurified by HPLC

Sources & evidence

ORD record
ord-5b2441d0715a472bbb05d45d51a52c4c
Source dataset
uspto-grants-2008_12
Patent number
US07462639B2

Reaction notes

Loading…