Ethanol → HCID 87605692, compound

HRID 1983853Notes

Reaction equation

HRID 1983853 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:28]3[CH:29]=[C:30](/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37])[CH:31]=[CH:32][CH:33]=3)=[C:7]([CH2:13][C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[C:24]([F:27])([F:26])[F:25])=[O:15])[C:8](=[O:12])[O:9]2)=[CH:4][C:3]=1[CH3:39].[OH:40][CH2:41][C:42]([CH2:46][OH:47])([CH2:44][OH:45])[NH2:43].C(O)C>C(#N)C>[OH:40][CH2:41][C:42]([CH2:46][OH:47])([CH2:44][OH:45])[NH2:43].[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:28]3[CH:29]=[C:30](/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37])[CH:31]=[CH:32][CH:33]=3)=[C:7]([CH2:13][C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[C:24]([F:25])([F:27])[F:26])=[O:15])[C:8](=[O:12])[O:9]2)=[CH:4][C:3]=1[CH3:39]

Participants

5

Reactant 3

HCID 702EthanolHCID 6503Tris(hydroxymethyl)aminomethaneHCID 11227728HCID 11227728, compound

Product 1

HCID 87605692HCID 87605692, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
70 °C

Procedure

A mixture of (2E)-3-{3-[7-chloro-3-(2-{[4-fluoro-2-(trifluoromethyl)phenyl]amino}-2-oxoethyl)-6-methyl-2-oxo-2H-chromen-4-yl]phenyl}acrylic acid (10.0 g), tris(hydroxymethyl)methylamine (2.2 g), ethanol (70 ml) and acetonitrile (100 ml) was heated and stirred at 70° C. to dissolve the mixture. Acetonitrile (200 ml) was slowly added to the reaction mixture, and the mixture was stirred at 70° C. for 3 hours, gradually cooled to room temperature, and then stirred at room temperature overnight. Crystals obtained were collected by filtration, washed with acetonitrile, and dried at 60° C. for 8 hours under reduced pressure to obtain the title compound as colorless crystals (10.5 g, yield 86%). The crystals obtained showed the X-ray powder diffraction pattern as shown in FIG. 3 and crystallinity was 64%.

Workup

  1. temperaturewas heated
  2. dissolutionto dissolve the mixture
  3. stirringthe mixture was stirred at 70° C. for 3 hours
  4. temperaturegradually cooled to room temperature
  5. stirringstirred at room temperature overnight
  6. customCrystals obtained
  7. filtrationwere collected by filtration
  8. washwashed with acetonitrile
  9. customdried at 60° C. for 8 hours under reduced pressure

Sources & evidence

ORD record
ord-5c1f0527f0ed43b19d8bee4ea65582cc
Source dataset
uspto-grants-2009_06
Patent number
US07541478B2

Reaction notes

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