4-Methylmorpholine → HCID 22031972, compound

HRID 1792522Notes

Reaction equation

HRID 1792522 reaction equation
C[N:2]1[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.O.ON1C2C=CC=CC=2N=N1.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[N:29]2[CH:30]=[C:31]([C:34]3[C:35]([C:58]4[CH:66]=[CH:65][C:61]([C:62](O)=[O:63])=[CH:60][CH:59]=4)=[N:36][N:37]([C:39]([C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[CH:38]=3)[CH:32]=[CH:33][C:28]2=[N:27][CH:26]=1.N1CCOCC1.Cl.C(N=C=NCCCN(C)C)C>O.C(OCC)(=O)C.CN(C)C=O>[O:5]1[CH2:6][CH2:7][N:2]([C:62]([C:61]2[CH:60]=[CH:59][C:58]([C:35]3[C:34]([C:31]4[CH:32]=[CH:33][C:28]5[N:29]([C:25]([C:20]6[CH:21]=[CH:22][CH:23]=[CH:24][N:19]=6)=[CH:26][N:27]=5)[CH:30]=4)=[CH:38][N:37]([C:39]([C:46]4[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=4)([C:52]4[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=4)[C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)[N:36]=3)=[CH:66][CH:65]=2)=[O:63])[CH2:3][CH2:4]1

Participants

9

Reactant 5

HCID 79724-MethylmorpholineHCID 8083MorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22031009HCID 22031009, compound

Product 1

HCID 22031972HCID 22031972, compoundYield 93.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

17 mg N-methyl morpholine and 13 mg 1-hydroxy-1H-benzotriazole monohydrate were added in this order at room temperature to a mixture of 50 mg 4-{4-[3-(2-pyridyl)imidazo[1,2-a]pyridin-6-yl]-1-trityl-1H-3-pyrazolyl} benzoic acid obtained in Example 46, 7.7 mg morpholine, 17 mg 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride and 8 mL N,N-dimethylformamide. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated, washed twice with water and then with brine and dried over anhydrous sodium sulfate. The drying agent was filtered off, the filtrate was evaporated, and the residue was purified by NH silica gel column chromatography (hexane/ethyl acetate) to give 52 mg of the title compound as a colorless amorphous.

Workup

  1. customthe organic layer was separated
  2. washwashed twice with water
  3. dry with materialwith brine and dried over anhydrous sodium sulfate
  4. filtrationThe drying agent was filtered off
  5. customthe filtrate was evaporated
  6. customthe residue was purified by NH silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1612ef01a6a24b24a4a1a3a81af688e4
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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