Morpholine → HCID 66636096, compound

HRID 44265Notes

Reaction equation

HRID 44265 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([C:10]([OH:12])=O)=[CH:7][NH:8][CH:9]=1)=[O:4].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:46]1[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1>CN(C=O)C.C(Cl)Cl.[OH-].[Na+]>[N:46]1([C:10]([C:6]2[C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:9][NH:8][CH:7]=2)=[O:12])[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1

Participants

8

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 54027374HCID 54027374, compound

Product 1

HCID 66636096HCID 66636096, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4-(methoxycarbonyl)-1H-pyrrole-3-carboxylic acid (2.35 g) in DMF (49 ml) there are added diisopropylethylamine (2.11 ml) and HATU (4.9 ml). After stirring for 15 minutes at 40° C., morpholine (1.35 ml) is added. After stirring for 9 hours at 60° C. and at ambient temperature over a weekend, the mixture is diluted with CH2Cl2 and 1N sodium hydroxide solution. The aqueous phase is extracted 3 times with CH2Cl2 and the organic phases are combined. The organic phase is dried over magnesium sulphate, filtered and evaporated to dryness to yield the title product, which is used directly in the next Step.

Workup

  1. stirringAfter stirring for 9 hours at 60° C. and at ambient temperature over a weekend
  2. extractionThe aqueous phase is extracted 3 times with CH2Cl2
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-a1fa8d15b0d04a0e9b8a50985141ba7b
Source dataset
uspto-grants-2013_09
Patent number
US08541412B2

Reaction notes

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