Potassium Carbonate → HCID 11613268, compound

HRID 1785946Notes

Reaction equation

HRID 1785946 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]([CH2:23][CH2:24][CH2:25][CH2:26][C:27](OCC)=[O:28])=[CH:19][CH:18]=2)=[O:16])[C@@H:7]([CH3:32])[CH2:6]1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C[N:47](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl-].[NH4+]>CO.CN(C=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:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH2:26][C:27]([NH2:47])=[O:28])=[CH:19][CH:18]=2)=[O:16])[C@@H:7]([CH3:32])[CH2:6]1)(=[O:3])[CH3:2]

Participants

9

Reactant 6

HCID 11430Potassium CarbonateHCID 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 68918360HCID 68918360, compound

Product 1

HCID 11613268HCID 11613268, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

Ethyl 5-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenyl)pentanoate (0.135 g, 0.25 mmol) was hydrolyzed to the acid by dissolving in 6 ml methanol and potassium carbonate (0.2 g in 4 ml water) was added. The mixture was heated to 40° C. for 24 hours and methanol was removed in vacuo. The mixture was acidified to form a white precipitate. The solid was filtered to give the acid. To a solution of the acid in DMF (10 mL) at room temperature was added HATU (0.143 g, 0.375 mmol), DIEA (0.18 mL, 1 mmol), HOBt (0.057 g, 0.375 mmol), and ammonium chloride (0.027 g, 0.5 mmol) was added. The mixture was stirred for 18 hours and concentrated. The residue was dissolved in CH2Cl2 and washed with water. The organic layer was concentrated and purified by silica gel chromatography (87% CH2Cl2/13% methanol) to afford 5-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenyl)pentanamide.

Workup

  1. custommethanol was removed in vacuo
  2. customto form a white precipitate
  3. filtrationThe solid was filtered
  4. customto give the acid
  5. additionwas added
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in CH2Cl2
  8. washwashed with water
  9. concentrationThe organic layer was concentrated
  10. custompurified by silica gel chromatography (87% CH2Cl2/13% methanol)

Sources & evidence

ORD record
ord-3128afadddc3442999db123be835d0e1
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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