Pyrrolidine → HCID 10116404, compound

HRID 1593946Notes

Reaction equation

HRID 1593946 reaction equation
Cl[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:20]=[CH:19][C:18]2[NH:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:21][C:22](=[O:26])[CH2:23][CH2:24]Cl)[CH:15]=3)[C:10](=[O:27])[C:9]=2[CH:8]=1)=[O:5].[NH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1>CN(C)C=O.C(O)C>[N:28]1([CH2:2][CH2:3][C:4]([NH:6][C:7]2[CH:20]=[CH:19][C:18]3[NH:17][C:16]4[C:11](=[CH:12][CH:13]=[C:14]([NH:21][C:22](=[O:26])[CH2:23][CH2:24][N:28]5[CH2:32][CH2:31][CH2:30][CH2:29]5)[CH:15]=4)[C:10](=[O:27])[C:9]=3[CH:8]=2)=[O:5])[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 58780842HCID 58780842, compound

Product 1

HCID 10116404HCID 10116404, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

2,6-Bis(3-chloropropionamido)-9(10H)-acridone (AR-ACO-9, 3.00 g, 7.38 mmol) and KI (0.10 g, 0.60 mmol) were suspended in a mixture of dimethylformamide (45 mL) and ethanol (45 mL). Pyrrolidine (12 mL, 10.22 g, 144 mmol) was added in one lot and the whole stirred at reflux for 21 hr. The flask was cooled and all the solvents removed under reduced pressure. Dimethylformamide (100 mL) was added to the flask and this was in turn removed under reduced pressure. The process was repeated with toluene (2×100 mL) and propan-2-ol (2×100 mL). The solid in the flask was dissolved in water (60 mL) and 0.88 s.g. ammonia (10 mL) was added dropwise with stirring to yield an orange-brown precipitate. The flask was chilled with ice-water and the product collected, washed with dilute ammonia (2×10 mL, 1% dilution of 0.88 s.g. ammonia) and ice-cold water (2×10 mL). The product was dried in air and over P2O5 under vacuum to yield a yellow solid AR-ACO-10 (3.11 g, 87%).

Workup

  1. temperatureat reflux for 21 hr
  2. temperatureThe flask was cooled
  3. customall the solvents removed under reduced pressure
  4. additionDimethylformamide (100 mL) was added to the flask
  5. customremoved under reduced pressure
  6. dissolutionThe solid in the flask was dissolved in water (60 mL) and 0.88 s
  7. additionammonia (10 mL) was added dropwise
  8. stirringwith stirring
  9. customto yield an orange-brown precipitate
  10. customthe product collected
  11. washwashed with dilute ammonia (2×10 mL, 1% dilution of 0.88 s.g. ammonia) and ice-cold water (2×10 mL)
  12. dry with materialThe product was dried in air and over P2O5 under vacuum
  13. customto yield a yellow solid AR-ACO-10 (3.11 g, 87%)

Sources & evidence

ORD record
ord-f4daefbe248b48b78f7ff8e0e6f2323c
Source dataset
uspto-grants-2007_11
Patent number
US07300930B2

Reaction notes

Loading…