Diethyl Ether → HCID 67305487, compound

HRID 1009760Notes

Reaction equation

HRID 1009760 reaction equation
C(Cl)(=O)C(Cl)=O.[CH2:7]([N:9]1[CH:13]=[C:12]([NH:14][C:15](=[O:39])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[C:31]([C:34]([OH:36])=O)[CH:32]=4)[N:27]=[CH:26][CH:25]=3)=[CH:19][C:18]=2[O:37][CH3:38])[CH:11]=[N:10]1)[CH3:8].C(OCC)C.[CH3:45][NH2:46]>C(Cl)Cl>[CH2:7]([N:9]1[CH:13]=[C:12]([NH:14][C:15](=[O:39])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[C:31]([C:34](=[O:36])[NH:46][CH3:45])[CH:32]=4)[N:27]=[CH:26][CH:25]=3)=[CH:19][C:18]=2[O:37][CH3:38])[CH:11]=[N:10]1)[CH3:8]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6329MethylamineHCID 65578Oxalyl chlorideHCID 67304717HCID 67304717, compound

Product 1

HCID 67305487HCID 67305487, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (0.142 ml) was added to a mixture of N-(1-ethylpyrazol-4-yl)-2-[4-(6-carboxyquinolin-4-yloxy)-2-methoxyphenyl]acetamide (0.15 g) and methylene chloride (6 ml) and the resultant mixture was stirred at ambient temperature for 10 minutes. Diethyl ether (10 ml) was added and the resultant precipitate was recovered and dried under vacuum. The material so obtained was suspended in methylene chloride and methylamine gas was passed into the suspension until a clear solution was obtained. The solvent was evaporated and the residue was purified by column chromatography on silica using a gradient of 100:0 to 19:1 of methylene chloride and methanol as eluent. There was thus obtained the title compound (0.102 g); 1H NMR: (DMSOd6) 1.33 (t, 3H), 2.85 (d, 3H), 3.61 (s, 2H), 3.78 (s, 3H), 4.07 (q, 2H), 6.7 (d, 1H), 6.87 (m, 1H), 7.01 (d, 1H), 7.37 (d, 1H), 7.42 (s, 1H), 7.88 (s, 1H), 8.08 (d, 1H), 8.24 (m, 1H), 8.77 (d, 1H), 8.82 (q, 1H), 8.87 (d, 1H), 10.06 (s, 1H); Mass Spectrum: M+H+ 460.

Workup

  1. customthe resultant precipitate was recovered
  2. customdried under vacuum
  3. customThe material so obtained
  4. customwas obtained
  5. customThe solvent was evaporated
  6. customthe residue was purified by column chromatography on silica using a gradient of 100:0 to 19:1 of methylene chloride and methanol as eluent

Sources & evidence

ORD record
ord-e654c6da49284ce0add0067fb61ef841
Source dataset
uspto-grants-2011_07
Patent number
US07973164B2

Reaction notes

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