Dimethylformamide → HCID 9937573, compound

HRID 566901Notes

Reaction equation

HRID 566901 reaction equation
CN(C)C=O.Cl.Cl[CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.[NH2:16][C:17](=[O:48])[C:18]([C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[O:29][CH2:30][C:31]([OH:33])=[O:32])[N:22]([CH2:34][C:35]2[CH:36]=[C:37]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH:38]=[CH:39][CH:40]=2)[C:21]=1[CH3:47])=[O:19].[Na]>O>[NH2:16][C:17](=[O:48])[C:18]([C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[O:29][CH2:30][C:31]([O:33][CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[O:32])[N:22]([CH2:34][C:35]2[CH:36]=[C:37]([C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH:38]=[CH:39][CH:40]=2)[C:21]=1[CH3:47])=[O:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 5360545SodiumHCID 9955004HCID 9955004, compound

Product 1

HCID 9937573HCID 9937573, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

In a flask containing 10 ml of dimethylformamide was added with stirring 133 mg. of 4-(2-chloroethyl)morpholine hydrochloride (available from Aldrich Chemical Co., Milwaukee, Wis. USA, Item No. C4,220-3) and 231 mg. of CsCO3 and 300 mg. of ((3-(2-amino-1,2-dioxoethyl)-1-((1,1′-biphenyl)-3-ylmethyl)-2-methyl-1H-indol-4-yl)oxy)acetic acid, sodium salt. The slurry was heated to 60° C. until a solution formed. Heating was continued overnight until reaction was complete. 20 ml of H2O was added to the flask and the organic soluble phase extracted with three 20 ml. portions of ethyl acetate. The ethyl acetate solution was washed with water and dried over and dried over Na2SO4. Removal of solvent gave product verified by IR and NMR to be the title compound. Molecular Formula: C32H22N3O6

Workup

  1. additionwas added
  2. customformed
  3. temperatureHeating
  4. customwas continued overnight until reaction
  5. extractionthe organic soluble phase extracted with three 20 ml
  6. washThe ethyl acetate solution was washed with water
  7. customdried over and
  8. dry with materialdried over Na2SO4
  9. customRemoval of solvent
  10. customgave product

Sources & evidence

ORD record
ord-0bfea3f35ff84770b36796b1f6d3e0d2
Source dataset
uspto-grants-2001_01
Patent number
US06177426B1

Reaction notes

Loading…