Ethanol → HCID 86628834, compound

HRID 1009766Notes

Reaction equation

HRID 1009766 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(O)C.[CH3:36][S:37]([OH:40])(=[O:39])=[O:38]>C(OCC)(=O)C>[S:37]([OH:40])(=[O:39])(=[O:38])[CH3:36].[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 702Ethanol2×HCID 6395Methanesulfonic AcidHCID 24759089HCID 24759089, compound

Product 1

HCID 86628834HCID 86628834, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A stirred mixture of N-(1,3-dimethyl-1H-pyrazol-4-yl)-2-[2-methoxy-4-(7-methoxyquinolin-4-yloxy)phenyl]acetamide (1 g), ethyl acetate (16 ml) and ethanol (4 ml) was heated to reflux until a solution was obtained. The resultant solution was stirred and methanesulphonic acid (0.15 ml) was added dropwise. A precipitate started to form which was dissolved by the addition of ethanol (6 ml). Sufficient ethyl acetate was added until a slightly cloudy solution was formed. The resultant solution was filtered whilst hot and the filtrate was allowed to cool to ambient temperature. The mixture was allowed to stand at ambient temperature for 16 hours. The precipitate was collected by filtration and dried to constant weight under vacuum (1.3×10−4 atmospheres) at 50° C. during 24 hours. There was thus obtained the title salt (1 g); m.p. onset of melting at about 194° C. and a melting point peak at 206-213° C.; 1H NMR: (DMSOd6, at 24° C.) 2.13 (s, 3H), 2.31 (s 3H), 3.68 (s, 2H), 3.7 (s, 3H), 3.79 (s, 3H), 4.04 (s, 3H), 6.88 (d, 1H), 6.95 (m, 1H), 7.11 (d, 1H), 7.42 (d, 1H), 7.53 (d, 1H), 7.58 (m, 1H), 7.8 (s, 1H), 8.48 (d, 1H), 8.94 (d, 1H), 9.46 (s, 1H);

Workup

  1. temperaturewas heated
  2. temperatureto reflux until a solution
  3. customwas obtained
  4. customto form which
  5. customwas formed
  6. filtrationThe resultant solution was filtered whilst hot and the filtrate
  7. filtrationThe precipitate was collected by filtration
  8. customdried to constant weight under vacuum (1.3×10−4 atmospheres) at 50° C. during 24 hours

Sources & evidence

ORD record
ord-e27206c3b86241398b59f8512b523dc8
Source dataset
uspto-grants-2011_07
Patent number
US07973164B2

Reaction notes

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