tert-Butyl methyl ether → HCID 86628835, compound

HRID 1009767Notes

Reaction equation

HRID 1009767 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.O.[C:34]1([CH3:44])[CH:39]=[CH:38][C:37]([S:40]([OH:43])(=[O:42])=[O:41])=[CH:36][CH:35]=1.COC(C)(C)C>C(O)C>[C:34]1([CH3:44])[CH:35]=[CH:36][C:37]([S:40]([OH:43])(=[O:41])=[O:42])=[CH:38][CH:39]=1.[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 etherHCID 521998p-Toluenesulfonic acid monohydrateHCID 24759089HCID 24759089, compound

Product 1

HCID 86628835HCID 86628835, compoundYield 83.3%

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 (0.605 g) in ethanol (5 ml) was heated to reflux until a solution was obtained. The resultant solution was stirred and a solution of 4-toluenesulphonic acid monohydrate (0.333 g; 1.25 equivalents) in ethanol (95%, 5 ml) was added. The mixture was allowed to start to cool and tert-butyl methyl ether (12 ml) was added. 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 (0.705 g); m.p. 126-136° C.; 1H NMR: (DMSOd6, at 24° C.) 2.13 (s, 3H), 2.28 (s, 3H), 3.68 (s, 2H), 3.7 (s, 3H), 3.79 (s, 3H), 4.03 (s, 3H), 6.87 (d, 1H), 6.95 (m, 1H), 7.08-7.13 (m, 3H), 7.42 (d, 1H), 7.47 (d, 2H), 7.51 (d, 1H), 7.58 (m, 1H), 7.8 (s, 1H), 8.47 (d, 1H), 8.93 (d, 1H), 9.46 (s, 1H);

Workup

  1. temperaturewas heated
  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-75764876576a4ee799986f71ee7dd01b
Source dataset
uspto-grants-2011_07
Patent number
US07973164B2

Reaction notes

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