Ammonium Chloride → HCID 57595419, compound

HRID 1785995Notes

Reaction equation

HRID 1785995 reaction equation
[C:1]([N:4]([C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=1)[C@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]([C:17]2[CH:22]=[CH:21][C:20](N3CCC(C(O)=O)CC3)=[CH:19][CH:18]=2)=[O:16])[C@@H:7]([CH3:32])[CH2:6]1)(=[O:3])[CH3:2].C1C=CC2N([OH:49])N=NC=2C=1.CN(C(ON1N=N[C:60]2[CH:61]=[CH:62][CH:63]=[N:64][C:59]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C([N:77]([CH:80](C)C)CC)(C)C.[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C>[C:1]([N:4]([C:33]1[CH:34]=[CH:35][C:36]([Cl:39])=[CH:37][CH:38]=1)[C@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]([C:17]2[CH:18]=[CH:19][C:20]([N:64]3[CH2:59][CH2:60][CH:61]([C:80]([NH2:77])=[O:49])[CH2:62][CH2:63]3)=[CH:21][CH:22]=2)=[O:16])[C@@H:7]([CH3:32])[CH2:6]1)(=[O:3])[CH3:2]

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57595422(2S,4R)-1-(4-{4-[acetyl(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-piperidine-4-carboxylic acid

Product 1

HCID 57595419HCID 57595419, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2S,4R)-1-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-piperidine-4-carboxylic acid amide was prepared from (2S,4R)-1-(4-{4-[acetyl(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-piperidine-4-carboxylic acid. The acid (0.120 g, 0.22 mmol) was dissolved in DMF (2.5 mL) at room temperature and HOBt (0.044 g, 0.33 mmol), HATU (0.125 g, 0.33 mol), and diisopropylethylamine (0.15 mL, 0.88 mmol) was added followed by ammonium chloride (0.024 g, 0.44 mmol) and stirred at room temperature for 16 h. The reaction was diluted with ethyl acetate, washed with 1N NaOH, 1N HCl and brine. The organics were dried over MgSO4, filtered and concentrated down. The crude residue was purified HPLC purification.

Workup

  1. washwashed with 1N NaOH, 1N HCl and brine
  2. dry with materialThe organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated down
  5. customThe crude residue was purified
  6. customHPLC purification

Sources & evidence

ORD record
ord-febfa0afe65845b4a5376e0a5e2deaa6
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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