Hydrochloric Acid → HCID 71239397, compound

HRID 2281163Notes

Reaction equation

HRID 2281163 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][CH2:6][NH:7][C:8](=[O:35])[C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH:29]2[CH2:32][C:31]([CH3:34])([CH3:33])[CH2:30]2)[NH:16][C:17]2[C:26]([CH3:27])=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([F:28])[CH:23]=3)[N:18]=2)=[CH:11][CH:10]=1)C.[OH-].[Na+].Cl>O1CCCC1.CO>[CH3:33][C:31]1([CH3:34])[CH2:32][CH:29]([CH:15]([NH:16][C:17]2[C:26]([CH3:27])=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([F:28])[CH:23]=3)[N:18]=2)[C:12]2[CH:11]=[CH:10][C:9]([C:8]([NH:7][CH2:6][CH2:5][C:4]([OH:36])=[O:3])=[O:35])=[CH:14][CH:13]=2)[CH2:30]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71239892HCID 71239892, compound

Product 1

HCID 71239397HCID 71239397, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(+/−)-3-{4-[(3,3-Dimethyl-cyclobutyl)-(6-fluoro-3-methyl-quinolin-2-ylamino)-methyl]-benzoylamino}-propionic acid ethyl ester (14.3 mg, 0.029 mmol), made in a similar manner as Intermediate 27 from Intermediate 29, was dissolved in tetrahydrofuran (1.5 mL) and methanol (0.5 mL), and 1.0 M sodium hydroxide (1 mL) was added. This was stirred as a solution at room temperature for 20 min before 1 N HCl was added to bring to pH 5. This was extracted twice with ethyl acetate and the combined organics dried over MgSO4, and concentrated in vacuo. Purification by reversed-phase HPLC gave (+/−)-3-{4-[(3,3-dimethyl-cyclobutyl)-(6-fluoro-3-methyl-quinolin-2-ylamino)-methyl]-benzoylamino}-propionic acid (10 mg). Analytical LCMS: retention time 2.3998 minutes (Waters Atlantic dC18 4.6×50 mm, 5 μm column; 5% acetonitrile/water (0.05% trifluoroacetic acid modifier) linear gradient to 95% acetonitrile/water over 4.0 minutes, hold at 95% acetonitrile/water for 1.0 minute; flow rate 2.0 mL/minute); MS (M+1): 464.0.

Workup

  1. additionwas added
  2. extractionThis was extracted twice with ethyl acetate
  3. dry with materialthe combined organics dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification by reversed-phase HPLC

Sources & evidence

ORD record
ord-bef2aca4d59b4b93a09951c471a41d9b
Source dataset
uspto-grants-2015_09
Patent number
US09139538B2

Reaction notes

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