Ammonium Chloride → HCID 178513936, compound

HRID 1778239Notes

Reaction equation

HRID 1778239 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=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][CH:21]2[CH2:26][CH2:25][N:24]([C:27](=[O:32])[CH2:28][C:29]([OH:31])=O)[CH2:23][CH2:22]2)=[CH:4][CH:3]=1.[NH4+].[Cl-].CC[N:44](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:39][C:36]1[CH:35]=[CH:34][C:33]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=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][CH:21]2[CH2:26][CH2:25][N:24]([C:27](=[O:32])[CH2:28][C:29]([NH2:44])=[O:31])[CH2:23][CH2:22]2)=[CH:38][CH:37]=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 178525627HCID 178525627, compound

Product 1

HCID 178513936HCID 178513936, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Into a 8-mL vial, was placed 3-[4-([6-[bis(4-chlorophenyl)methyl]-2-hydroxyquinolin-4-yl]amino)piperidin-1-yl]-3-oxopropanoic acid (20 mg, 0.03 mmol, 1.00 equip, 98%), NH4Cl (9.48 mg, 0.18 mmol, 5.00 equip), DIEA (45.7 mg, 0.35 mmol, 10.00 equip, 99%), HATU (20.2 mg, 0.05 mmol, 1.50 equip, 99%), and N,N-dimethylformamide (3 mL). The resulting solution was stirred overnight at room temperature. The resulting solution was diluted with water (20 mL). The resulting solution was extracted with ethyl acetate (3×20 mL) and the organic layers combined. The resulting mixture was washed with water (1×20 mL) and brine (1×20 mL). The resulting mixture was dried over anhydrous sodium sulfate. The solids were filtered out. The residue was applied onto a silica gel column with dichloromethane/methanol (10:1) to yield 3-[4-([6-[bis(4-chlorophenyl)methyl]-2-hydroxyquinolin-4-yl]amino)piperidin-1-yl]-3-oxopropanamide as a white solid.

Workup

  1. extractionThe resulting solution was extracted with ethyl acetate (3×20 mL)
  2. washThe resulting mixture was washed with water (1×20 mL) and brine (1×20 mL)
  3. dry with materialThe resulting mixture was dried over anhydrous sodium sulfate
  4. filtrationThe solids were filtered out

Sources & evidence

ORD record
ord-9446401e475d4f9aa755f3225730999e
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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