4-Methylmorpholine → HCID 18412459, compound

HRID 50203Notes

Reaction equation

HRID 50203 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[N:6][C:7]([C:11](O)=[O:12])=[CH:8][CH:9]=2)[N:4]=[C:3]1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=1.CN1CCOCC1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[N:53]1[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=1[NH:59][CH2:60][CH2:61][C:62]([O:64][CH3:65])=[O:63]>CN(C)C=O>[N:53]1[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=1[N:59]([CH2:60][CH2:61][C:62]([O:64][CH3:65])=[O:63])[C:11]([C:7]1[N:6]=[C:5]2[N:4]=[C:3]([CH2:14][O:15][C:16]3[CH:17]=[CH:18][C:19]([C:22]#[N:23])=[CH:20][CH:21]=3)[N:2]([CH3:1])[C:10]2=[CH:9][CH:8]=1)=[O:12]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 818199Methyl N-pyridin-2-yl-beta-alaninateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 18412598HCID 18412598, compound

Product 1

HCID 18412459HCID 18412459, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

308 mg (1.0 mmol) of 1-methyl-2-[(4-cyanophenyl)oxymethyl]-5-carboxyimidazo[4,5-b]pyridine were suspended in 5 mL of dimethylformamide and mixed with 303 mg (3.0 mmol) of N-methylmorpholine and 321 mg (1.0 mmol) of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate. After 10 minutes at room temperature, a solution of 215 mg (1.2 mmol) of methyl N-(2-pyridyl)-3-aminopropionate in 2 mL of dimethylformamide was added, whereupon a clear solution was obtained. After 12 hours at room temperature, the reaction solution was stirred into ice-water. After extracting 3 times with ethyl acetate, the combined organic extracts were washed with a saline solution, dried over sodium sulfate, and evaporated down. The residue obtained was chromatographed on silica gel with dichloromethane/ethanol (90:1 to 25:1). Yield: 165 mg of white powder (35% of theory), C25H12N6O4 (407.50); melting point: 139° C.-140° C.

Workup

  1. customwas obtained
  2. waitAfter 12 hours at room temperature
  3. extractionAfter extracting 3 times with ethyl acetate
  4. washthe combined organic extracts were washed with a saline solution
  5. dry with materialdried over sodium sulfate
  6. customevaporated down
  7. customThe residue obtained
  8. customwas chromatographed on silica gel with dichloromethane/ethanol (90:1 to 25:1)

Sources & evidence

ORD record
ord-a03bc704707940258cba8f41bca2b0e9
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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