tert-Butyl methyl ether → HCID 67305015, compound

HRID 1009765Notes

Reaction equation

HRID 1009765 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8](=[O:31])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]3[C:26]4[C:21](=[CH:22][C:23]([O:27][CH3:28])=[CH:24][CH:25]=4)[N:20]=[CH:19][CH:18]=3)=[CH:12][C:11]=2[O:29][CH3:30])[C:4]([CH3:32])=[N:3]1.[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]\[C:36]([OH:38])=[O:37].COC(C)(C)C>C(O)C>[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]\[C:36]([OH:38])=[O:37].[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8](=[O:31])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]3[C:26]4[C:21](=[CH:22][C:23]([O:27][CH3:28])=[CH:24][CH:25]=4)[N:20]=[CH:19][CH:18]=3)=[CH:12][C:11]=2[O:29][CH3:30])[C:4]([CH3:32])=[N:3]1

Participants

5

Reactant 3

HCID 15413tert-Butyl methyl ether2×HCID 444266Maleic AcidHCID 24759089HCID 24759089, compound

Product 1

HCID 67305015HCID 67305015, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A stirred suspension of N-(1,3-dimethyl-1H-pyrazol-4-yl)-2-[2-methoxy-4-(7-methoxyquinolin-4-yloxy)phenyl]acetamide (0.608 g) in ethanol (5 ml) was heated gently to reflux until a solution was obtained. The resultant solution was stirred and a solution of maleic acid (0.18 g; 1.07 equivalents) in ethanol (95%, 5 ml) was added. The mixture was allowed to start to cool and tert-butyl methyl ether (5 ml) was added. When the mixture had cooled to ambient temperature, a second portion (5 ml) of tert-butyl methyl ether was added and the resultant mixture was allowed to stand at ambient temperature for 29 hours. The precipitate was collected by filtration and dried to constant weight under vacuum (1.3×10−4 atmospheres) at 50° C. during 4 hours. There was thus obtained the title salt (0.688 g); m.p. 192-199° C.; 1H NMR: (DMSOd6, at 24° C.) 2.12 (s, 3H), 3.66 (s, 2H), 3.7 (s, 3H), 3.78 (s, 3H), 3.97 (s, 3H), 6.19 (s, 2H), 6.63 (d, 1H), 6.84 (m, 1H), 7.0 (d, 1H), 7.35 (d, 1H), 7.38 (m, 1H), 7.44 (d, 1H), 7.81 (s, 1H), 8.29 (d, 1H), 8.72 (d, 1H), 9.44 (s, 1H);

Workup

  1. temperaturewas heated gently
  2. temperatureto reflux until a solution
  3. customwas obtained
  4. temperatureto cool
  5. filtrationThe precipitate was collected by filtration
  6. customdried to constant weight under vacuum (1.3×10−4 atmospheres) at 50° C. during 4 hours

Sources & evidence

ORD record
ord-79cd7da7a661411aa2ff5725a7ad54ed
Source dataset
uspto-grants-2011_07
Patent number
US07973164B2

Reaction notes

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