Dimethylformamide → HCID 12969097, compound

HRID 1266271Notes

Reaction equation

HRID 1266271 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[N:10]=2)[N:5]=[CH:4][C:3]=1[C:22]#[N:23].C(Cl)(=O)C([Cl:27])=O.CN(C=O)C>C(Cl)Cl>[Cl:27][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[N:10]=2)[N:5]=[CH:4][C:3]=1[C:22]#[N:23]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 178510311HCID 178510311, compound

Product 1

HCID 12969097HCID 12969097, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-hydroxy-6-(3-morpholin-4-yl-propoxy)-[1.5]naphthyridine-3-carbonitrile in anhydrous CH2Cl2 (150 ml) was added oxalyl chloride (2.7 ml, 31.8 mmol) and DMF (0.1 ml, 20%) at room temperature under nitrogen. The suspension became a clear dark brown solution. The resulting mixture was stirred for an additional 1 hr. The solvent was removed by rotary evaporation. The residue was dissolved in ice-water mixture, made basic with (NH4OH), and extracted with CH2Cl2. The extracts were washed (brine), dried (Na2SO4), and concentrated to give the title compound (400 mg, 38%). H-NMR δ (DMSO-d6): 1.88 (2H, m), 2.26-2.29 (6H, m), 2.51 (2H, m), 3.49 (2H, m), 4.34 (2H, m), 6.834 (1H, d, C7-H), 8.147 (1H, d, C8-H), 8.711 (1H, s, C2-H).

Workup

  1. customThe solvent was removed by rotary evaporation
  2. dissolutionThe residue was dissolved in ice-water mixture
  3. extractionextracted with CH2Cl2
  4. washThe extracts were washed (brine)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-26473c5c993845cd8127fe966da79bf5
Source dataset
uspto-grants-2003_04
Patent number
US06548496B2

Reaction notes

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