Morpholine → HCID 21913114, compound

HRID 1245975Notes

Reaction equation

HRID 1245975 reaction equation
[CH3:1][C:2]1[N:7]2[N:8]=[N:9][N:10]=[C:6]2[C:5]2[N:11]=[C:12]([CH2:29][CH2:30][CH3:31])[N:13]([CH2:14][CH2:15][CH2:16][S:17]([C:20]3[CH:28]=[CH:27][C:23]([C:24]([OH:26])=O)=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:4]=2[C:3]=1[CH3:32].C(Cl)(=O)C(Cl)=O.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1>ClCCl>[CH3:1][C:2]1[N:7]2[N:8]=[N:9][N:10]=[C:6]2[C:5]2[N:11]=[C:12]([CH2:29][CH2:30][CH3:31])[N:13]([CH2:14][CH2:15][CH2:16][S:17]([C:20]3[CH:28]=[CH:27][C:23]([C:24]([N:39]4[CH2:44][CH2:43][O:42][CH2:41][CH2:40]4)=[O:26])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:4]=2[C:3]=1[CH3:32]

Participants

5

Reactant 3

HCID 8083Morpholine2×HCID 65578Oxalyl chlorideHCID 21913806HCID 21913806, compound

Product 1

HCID 21913114HCID 21913114, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, a mixture of 4-[3-(5,6-dimethyl-8-propyl-7H-imidazo[4,5-c]tetrazolo[1,5-a]pyridin-7-yl)propane-1-sulfonyl]benzoic acid (2.26 g, 4.95 mmol) and dichloromethane (50 mL) was cooled to 0° C. Oxalyl chloride (0.95 mL, 10.9 mmol) was added dropwise, and the reaction was stirred for two hours at room temperature. To one-third of the solution was added morpholine (0.43 mL, 4.9 mmol), and the reaction was stirred under nitrogen overnight. Additional morpholine (1.0 mL, 11 mmol) was added, and the reaction was stirred for two hours. A white precipitate formed, which was isolated by filtration, washed with ethyl acetate and water, and then dried for two hours in a vacuum oven at 80° C. to provide 0.75 g of {4-[3-(5,6-dimethyl-8-propyl-7H-imidazo[4,5-c]tetrazolo[1,5-a]pyridin-7-yl)propane-1-sulfonyl]phenyl}morpholin-4-ylmethanone as a white solid.

Workup

  1. stirringthe reaction was stirred under nitrogen overnight
  2. stirringthe reaction was stirred for two hours
  3. customA white precipitate formed
  4. customwhich was isolated by filtration
  5. washwashed with ethyl acetate and water
  6. customdried for two hours in a vacuum oven at 80° C.

Sources & evidence

ORD record
ord-aa4550f1a8cf443c83948498c3ee6509
Source dataset
uspto-grants-2006_10
Patent number
US07125890B2

Reaction notes

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