Sodium Hydroxide → HCID 60151513, compound

HRID 537515Notes

Reaction equation

HRID 537515 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][N:10]([C:12]3[N:17]=[CH:16][C:15]([NH:18][CH:19]([C:23]4[CH:37]=[CH:36][C:26]([C:27]([NH:29][CH2:30][CH2:31][C:32]([O:34]C)=[O:33])=[O:28])=[CH:25][CH:24]=4)[CH2:20][CH2:21][CH3:22])=[CH:14][CH:13]=3)[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO.O1CCCC1>[C:1]1([C:7]2[CH:8]=[N:9][N:10]([C:12]3[N:17]=[CH:16][C:15]([NH:18][CH:19]([C:23]4[CH:24]=[CH:25][C:26]([C:27]([NH:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[O:28])=[CH:36][CH:37]=4)[CH2:20][CH2:21][CH3:22])=[CH:14][CH:13]=3)[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68157897HCID 68157897, compound

Product 1

HCID 60151513HCID 60151513, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-(4-(1-(6-(4-phenyl-1H-pyrazol-1-yl)pyridine-3-ylamino)butyl)benzamido)propanoate (82.1 mg, 0.165 mmol) was dissolved in methanol (0.5 mL) and tetrahydrofuran (0.5 mL). 1N Sodium hydroxide (0.33 mL) was added and the reaction was stirred at room temperature for 24 hours. The reaction was then concentrated. The crude residue was taken up in water and acidified with 1N hydrochloric acid to pH=3. A white precipitate formed. The solids were filtered off and dried under vacuum to give (+/−)-3-(4-(1-(6-(4-phenyl-1H-pyrazol-1-yl)pyridine-3-ylamino)butyl)benzamido)propanoic acid (61.6 mg, 77%) as an off-white solid. 1H NMR (400 MHz, CD3OD, δ): 8.57 (d, J=1.0 Hz, 1H), 7.96 (d, J=0.8 Hz, 1H), 7.78-7.69 (m, 3H), 7.61-7.50 (m, 3H), 7.47 (d, J=8.4 Hz, 2H), 7.38-7.31 (m, 2H), 7.24-7.16 (m, 1H), 7.05 (dd, J=8.9, 3.0 Hz, 1H), 4.48-4.41 (m, 1H), 3.63-3.55 (m, 2H), 2.60 (t, J=6.9 Hz, 2H), 1.94-1.69 (m, 2H), 1.58-1.33 (m, 2H), 0.96 (t, J=7.4 Hz, 3H). MS (M+1): 484.4.

Workup

  1. concentrationThe reaction was then concentrated
  2. customA white precipitate formed
  3. filtrationThe solids were filtered off
  4. customdried under vacuum

Sources & evidence

ORD record
ord-c68f71e0a3f74255afb3f8e991c301c7
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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