Ammonium Chloride → HCID 178514047, compound

HRID 1778244Notes

Reaction equation

HRID 1778244 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[C:14]([OH:19])[CH:13]=[C:12]3[NH:20][C:21]2[CH:31]=[CH:30][C:24]([O:25][CH2:26][C:27]([OH:29])=O)=[CH:23][CH:22]=2)=[CH:4][CH:3]=1.[NH4+].[Cl-].CC[N:43](C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>O.CN(C)C=O>[Cl:38][C:35]1[CH:34]=[CH:33][C:32]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[C:14]([OH:19])[CH:13]=[C:12]3[NH:20][C:21]2[CH:31]=[CH:30][C:24]([O:25][CH2:26][C:27]([NH2:43])=[O:29])=[CH:23][CH:22]=2)=[CH:37][CH:36]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178525963HCID 178525963, compound

Product 1

HCID 178514047HCID 178514047, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Into a 25-mL round-bottom flask, was placed 2-[4-([6-[bis(4-chlorophenyl)methyl]-2-hydroxyquinolin-4-yl]amino)phenoxy]acetic acid (30 g, 53.90 mmol, 1.00 equip, 98%), NH4Cl (14.72 mg, 0.27 mmol, 5.00 equip, 98%), DIPEA (71 mg, 0.54 mmol, 10.00 equip, 98%), HATU (31.37 mg, 0.08 mmol, 1.50 equip, 98%), and N,N-dimethylformamide (5 mL). The resulting solution was stirred overnight at room temperature. The resulting solution was diluted with water (50 mL). The resulting solution was extracted with ethyl acetate (3×50 mL) and the organic layers combined. The resulting mixture was washed with water (1×50 mL) and brine (1×50 mL). The resulting mixture was dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. The resulting residue was recrystallized from ethyl acetate:n-hexane in a ratio of 1:20 to yield 2-[4-([6-[bis(4-chlorophenyl)methyl]-2-hydroxyquinolin-4-yl]amino)phenoxy]acetamide as an off-white solid.

Workup

  1. customInto a 25-mL round-bottom flask, was placed
  2. extractionThe resulting solution was extracted with ethyl acetate (3×50 mL)
  3. washThe resulting mixture was washed with water (1×50 mL) and brine (1×50 mL)
  4. dry with materialThe resulting mixture was dried over anhydrous sodium sulfate
  5. filtrationThe solids were filtered out
  6. concentrationThe resulting mixture was concentrated under vacuum
  7. customThe resulting residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-727ece8b85c249b6a1bea5197ba38db3
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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