2-Methoxyethylamine → N6-(2-Methoxyethyl)-4-(3-chloro-4-{[(cyclopropylamino)carbonyl]amino}phenoxy)-7-(2-methoxyethoxy)-6-quinolinecarboxamide

HRID 853382Notes

Reaction equation

HRID 853382 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[NH:27][C:28]([NH:30][CH:31]1[CH2:33][CH2:32]1)=[O:29])[O:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:19][CH2:20][CH2:21][O:22][CH3:23])=[C:13]([C:16]([OH:18])=O)[CH:14]=2)[N:9]=[CH:8][CH:7]=1.[CH3:34][O:35][CH2:36][CH2:37][NH2:38].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(OCC)(=O)C.O.CN(C)C=O>[CH3:34][O:35][CH2:36][CH2:37][NH:38][C:16]([C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][C:12]=1[O:19][CH2:20][CH2:21][O:22][CH3:23])[N:9]=[CH:8][CH:7]=[C:6]2[O:5][C:4]1[CH:24]=[CH:25][C:26]([NH:27][C:28]([NH:30][CH:31]2[CH2:32][CH2:33]2)=[O:29])=[C:2]([Cl:1])[CH:3]=1)=[O:18]

Participants

8

Reactant 4

HCID 80182-MethoxyethylamineHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 589311914-(3-Chloro-4-{[(cyclopropylamino)carbonyl]amino)phenoxy)-7-(2-methoxyethoxy)-6-quinolinecarboxylic acid

Product 1

HCID 58930857N6-(2-Methoxyethyl)-4-(3-chloro-4-{[(cyclopropylamino)carbonyl]amino}phenoxy)-7-(2-methoxyethoxy)-6-quinolinecarboxamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(3-Chloro-4-{[(cyclopropylamino)carbonyl]amino}phenoxy)-7-(2-methoxyethoxy)-6-quinolinecarboxylic acid (200 mg), 2-methoxyethylamine (38 mg), benzotriazol-1-yloxytris (dimethylamino)phosphonium hexafluorophosphate (Bop reagent) (230 mg), triethylamine (0.12 ml) and dimethylformamide (5 ml) were stirred together at room temperature for 14 hours. Water and ethyl acetate were added to the reaction solution for extraction, NH type silica gel was added to the extract, the solvent was distilled off under reduced pressure and the reaction product was adsorbed onto the silica gel. The silica gel was charged into a dry column packed with NH type silica gel, and column purification was performed (ethyl acetate). The solvent was distilled off under reduced pressure to obtain 120 mg of the target substance as a solid.

Workup

  1. additionwas added to the extract
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionThe silica gel was charged into a dry column
  4. custompacked with NH type silica gel, and column purification
  5. distillationThe solvent was distilled off under reduced pressure
  6. customto obtain 120 mg of the target substance as a solid

Sources & evidence

ORD record
ord-cb002d3aab0f4f0395f2832204df4e4e
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

Loading…