tert-Butyl methyl ether → HCID 67304993, compound

HRID 1009764Notes

Reaction equation

HRID 1009764 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]([OH:46])(=[O:45])[CH2:35][C:36]([CH2:41][C:42]([OH:44])=[O:43])([C:38]([OH:40])=[O:39])[OH:37].COC(C)(C)C>C(O)C>[C:34]([OH:46])(=[O:45])[CH2:35][C:36]([CH2:41][C:42]([OH:44])=[O:43])([C:38]([OH:40])=[O:39])[OH: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 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 24759089HCID 24759089, compound

Product 1

HCID 67304993HCID 67304993, compoundYield 97.4%

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 (0.54 g) in ethanol (5 ml) was heated gently to reflux until a solution was obtained. The resultant solution was stirred and a solution of citric acid monohydrate (0.315 g; 1.2 equivalents) in ethanol (95%, 5 ml) was added. The mixture was allowed to start to cool and tert-butyl methyl ether (10 ml) was added. When the mixture had cooled to ambient temperature, a second portion (2 ml) of tert-butyl methyl ether was added and the resultant mixture was allowed to stand at ambient temperature for 28 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 (0.76 g); m.p. 209-212C; 1H NMR: (DMSOd6, at 24° C.) 2.12 (s, 3H), 2.65 (d, 2H), 2.75 (d, 2H), 3.64 (s, 2H), 3.7 (s, 3H), 3.78 (s, 3H), 3.94 (s, 3H), 6.53 (d, 1H), 6.79 (m, 1H), 6.96 (d, 1H), 7.3 (m, 1H), 7.32 (d, 1H), 7.41 (d, 1H), 7.81 (s, 1H), 8.21 (d, 1H), 8.63 (d, 1H), 9.43 (s, 1H), 12.39 (br s, 2H);

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-5d5697baff2f42efa3aaaa0c123a39dc
Source dataset
uspto-grants-2011_07
Patent number
US07973164B2

Reaction notes

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