Methylamine → HCID 86296660, compound

HRID 1748393Notes

Reaction equation

HRID 1748393 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17](O)=[O:18])[CH:13]=[N:14]2)=[CH:9][CH:8]=1.C(Cl)(=O)C(Cl)=O.[CH3:29][NH2:30]>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]([NH:30][CH3:29])=[O:18])[CH:13]=[N:14]2)=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 65578Oxalyl chlorideHCID 90417158HCID 90417158, compound

Product 1

HCID 86296660HCID 86296660, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-((3-chlorobenzyl)oxy)quinoline-3-carboxylic acid (50 mg, 0.16 mmol) in DCM (1.5 mL) was added oxalyl chloride (0.042 mL, 0.48 mmol) followed by 1 drop of DMF. After 30 minutes, methylamine (2M in THF, 1 mL, 2 mmol) was added to the reaction. The reaction was stirred for 14 h. The crude reaction was loaded directly onto a column and purification (FCC, SiO2, 0-10%, MeOH/DCM) afforded the title compound as a white solid (19 mg, 37%). 1H NMR (400 MHz, CDCl3) δ 9.17 (d, J=2.3 Hz, 1H), 8.53 (d, J=2.0 Hz, 1H), 7.82 (d, J=9.0 Hz, 1H), 7.49 (d, J=2.7 Hz, 2H), 7.38-7.31 (m, 4H), 6.28-6.22 (m, 1H), 5.21 (s, 2H), 3.10 (d, J=4.7 Hz, 3H). [M+H]=327.2.

Workup

  1. customThe crude reaction
  2. customwas loaded directly onto a column and purification (FCC, SiO2, 0-10%, MeOH/DCM)

Sources & evidence

ORD record
ord-4545b8f404134744bb8edee6ee83e773
Source dataset
uspto-grants-2015_10
Patent number
US09150572B2

Reaction notes

Loading…