Dimethylformamide → HCID 9937573, compound

HRID 1250918Notes

Reaction equation

HRID 1250918 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:49])[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[CH2:47]C)=[O:19].[Na]>O>[NH2:16][C:17](=[O:49])[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 70161363HCID 70161363, 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 is 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-ethyl-1H-indol-4-yl)oxy)acetic acid, sodium salt. The slurry is heated to 60° C. until a solution formed. Heating is continued overnight until reaction is complete. 20 ml of H2O is added to the flask and the organic soluble phase is extracted with three 20 ml. portions of ethyl acetate. The ethyl acetate solution is washed with water and dried over Na2SO4.

Workup

  1. additionis added
  2. customformed
  3. temperatureHeating
  4. customis continued overnight until reaction
  5. extractionthe organic soluble phase is extracted with three 20 ml
  6. washThe ethyl acetate solution is washed with water
  7. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-653d35240f77414c9d062d7c989acba1
Source dataset
uspto-grants-2002_01
Patent number
US06340699B1

Reaction notes

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