Hydrochloric Acid → HCID 46926794, compound

HRID 473967Notes

Reaction equation

HRID 473967 reaction equation
[OH-].[Na+].[CH3:3][C:4]([CH3:37])([CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:26]=[C:25]3[C:20]([C:21]([C:28](=[O:36])[NH:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:22][C:23]([CH3:27])=[N:24]3)=[CH:19][CH:18]=2)=[CH:13][N:12]=1)[C:5]([O:7]C)=[O:6].O1CCCC1.Cl>CO>[CH3:3][C:4]([CH3:37])([CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:26]=[C:25]3[C:20]([C:21]([C:28](=[O:36])[NH:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:22][C:23]([CH3:27])=[N:24]3)=[CH:19][CH:18]=2)=[CH:13][N:12]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 58577913HCID 58577913, compound

Product 1

HCID 46926794HCID 46926794, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1 N aqueous solution of sodium hydroxide (2.0 mL) was added to a solution of methyl 2,2-dimethyl-3-(5-(2-methyl-4-(phenylcarbamoyl)quinolin-7-yl)pyridin-2-yloxy)propanoate B-16 (94.0 mg, 0.20 mmol) in a 1:1 mixture of tetrahydrofuran:methanol (5.0 mL) at room temperature. After 12 h of stirring, the aqueous layer was acidified to pH 0 with a 1 N aqueous hydrogen chloride solution and concentrated to dryness under reduced pressure. The crude residue was purified by flash column chromatography on C18 reverse phase (water:acetonitrile gradient with 0.05% formic acid) to give 2,2-dimethyl-3-(5-(2-methyl-4-(phenylcarbamoyl)quinolin-7-yl)pyridin-2-yloxy)propanoic acid B-17 (54.7 mg, Yield=60%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.17 (s, 6H), 2.75 (s, 3H), 4.30 (s, 2H), 6.93 (d, J=8.5 Hz, 1H), 7.19 (t, J=7.5 Hz, 1H), 7.41 (t, J=9.5 Hz, 1H), 7.64 (s, 1H), 7.81 (d, J=8.0 Hz, 1H), 7.97 (d, J=9.0 Hz, 1H), 8.16 (d, J=8.5 Hz, 1H), 8.21 (d, J=8.5 Hz, 1H), 8.29 (s, 1H), 8.51 (s, 2H), 8.67 (m, 1H), 10.86 (s, 1H); MS (ESI) [M+1]+ 456.

Workup

  1. customat room temperature
  2. concentrationconcentrated to dryness under reduced pressure
  3. customThe crude residue was purified by flash column chromatography on C18 reverse phase (water:acetonitrile gradient with 0.05% formic acid)

Sources & evidence

ORD record
ord-adb5ce80fe0f4ea5ba0e8decc35c1bcd
Source dataset
uspto-grants-2014_01
Patent number
US08637507B2

Reaction notes

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