Ammonia → HCID 11274841, compound

HRID 1983856Notes

Reaction equation

HRID 1983856 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:28]3[CH:29]=[C:30]([CH2:34][CH2:35][CH2:36][C:37]([OH:39])=[O:38])[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[CH3:40].N.[Cl-].[Ca+2:43].[Cl-]>CC(C)=O.O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:28]3[CH:29]=[C:30]([CH2:34][CH2:35][CH2:36][C:37]([O-:39])=[O:38])[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[CH3:40].[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:28]3[CH:29]=[C:30]([CH2:34][CH2:35][CH2:36][C:37]([O-:39])=[O:38])[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[CH3:40].[Ca+2:43]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 5284359Calcium ChlorideHCID 11274842HCID 11274842, compound

Product 1

HCID 11274841HCID 11274841, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

To a solution of 4-{3-[7-chloro-3-(2-{[4-fluoro-2-(trifluoromethyl)phenyl]amino}-2-oxoethyl)-6-methyl-2-oxo-2H-chromen-4-yl]phenyl}butanoic acid obtained in Reference Example 9 (26.7 g, 0.0463 mol) in acetone (534 ml) was added 25% aqueous ammonia (4 ml) at 50° C., and the mixture was stirred at the same temperature for 15 minutes. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in a mixture of acetonitrile (534 ml) and water (107 ml). The reaction mixture was heated to 70° C., and a solution of calcium chloride (3.14 g, 0.0255 mol) in water (107 ml) was slowly added dropwise thereto. The reaction mixture was stirred at 70° C. for 3.5 hours, water (214 ml) was added thereto and the mixture was further stirred at 70° C. for 1 hour and at room temperature for 12 hours. Crystals obtained were collected by filtration, washed with water (100 ml) and dried at 50° C. under reduced pressure to obtain the title compound (26.67 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in a mixture of acetonitrile (534 ml) and water (107 ml)
  3. stirringThe reaction mixture was stirred at 70° C. for 3.5 hours
  4. stirringthe mixture was further stirred at 70° C. for 1 hour and at room temperature for 12 hours
  5. customCrystals obtained
  6. filtrationwere collected by filtration
  7. washwashed with water (100 ml)
  8. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-401a949ff67c41cabcd1009bc3091f77
Source dataset
uspto-grants-2009_06
Patent number
US07541478B2

Reaction notes

Loading…