4-Methylmorpholine → HCID 67050039, compound

HRID 217631

Reaction equation

HRID 217631 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:25][C:26]1[C:30]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[CH:29][S:28][CH:27]=1.[CH3:39][O:40][C:41]([C:43]1[CH:44]=[CH:45][C:46]([C:49](O)=[O:50])=[N:47][CH:48]=1)=[O:42].CN1CCOCC1>CN(C=O)C.C(OCC)(=O)C.O>[C:35]([O:34][C:32]([NH:31][C:30]1[C:26]([NH:25][C:49]([C:46]2[CH:45]=[CH:44][C:43]([C:41]([O:40][CH3:39])=[O:42])=[CH:48][N:47]=2)=[O:50])=[CH:27][S:28][CH:29]=1)=[O:33])([CH3:38])([CH3:37])[CH3:36]

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 3149925-(Methoxycarbonyl)pyridine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11063797HCID 11063797, compound

Product 1

HCID 67050039HCID 67050039, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

HATU (1.3 g, 3.5 mmol) was added to a solution of 3-amino-4-t-butoxycarbonylaminothiophene (Reference Compound No. 1-1, 0.68 g, 3.2 mmol), 5-methoxycarbonylpyridine-2-carboxylic acid (0.64 g, 3.5 mmol), and N-methylmorpholine (0.70 mL, 6.4 mmol) in DMF (20 mL), and then the reaction mixture was stirred at room temperature overnight. Water (0.30 L) and ethyl acetate (0.40 L) were added thereto, and the insoluble materials were filtered off to give 0.50 g of the title reference compound as a pale yellow solid. The filtrate was partitioned and the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and then the obtained solid was collected by filtration with ethylacetate (30 mL) to give 0.30 g of the title reference compound as a pale brown solid. (Yield 67%)

Workup

  1. filtrationthe insoluble materials were filtered off
  2. customto give 0.50 g of the title reference compound as a pale yellow solid
  3. customThe filtrate was partitioned
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. filtrationthe obtained solid was collected by filtration with ethylacetate (30 mL)
  7. customto give 0.30 g of the title reference compound as a pale brown solid

Sources & evidence

ORD record
ord-10d61d39493341c88cd84f7b81bfdad3
Source dataset
uspto-grants-2012_06
Patent number
US08198271B2

Linked notes

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