Lithium hydroxide, monohydrate → HCID 178432794, compound

HRID 1670677Notes

Reaction equation

HRID 1670677 reaction equation
O.[OH-].[Li+].[NH2:4][C:5]([C:7]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([C@H:19]3[CH2:24][CH2:23][C@H:22]([C:25]([O:27]C)=[O:26])[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)[C:10]([CH3:29])=[N:9][CH:8]=1)=[O:6]>CO.C1COCC1.O>[NH2:4][C:5]([C:7]1[N:12]=[C:11]([C:13]2[CH:14]=[CH:15][C:16]([C@H:19]3[CH2:20][CH2:21][C@H:22]([C:25]([OH:27])=[O:26])[CH2:23][CH2:24]3)=[CH:17][CH:18]=2)[C:10]([CH3:29])=[N:9][CH:8]=1)=[O:6]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 178501031HCID 178501031, compound

Product 1

HCID 178432794HCID 178432794, compoundYield 9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (42 mg, 1.00 mmol) was added to a stirred solution of methyl trans-4-{4-[6-(aminocarbonyl)-3-methylpyrazin-2-yl]phenyl}-cyclohexanecarboxylate (Example 65, 71 mg, 0.20 mmol) in MeOH (2 mL), THF (1 mL) and water (0.5 mL). After 16 h the reaction mixture was concentrated in vacuo and purified by reverse phase HPLC (150 mm×21 mm Phenomenex Column packed with Luna 10u C18 silica, eluting with 5-95% acetonitrile/water) to give the title compound as a yellow solid (6 mg, 9%); 1H NMR δ 9.01 (1H, s), 8.08 (1H, s), 7.73 (1H, s), 7.70 (2H, d), 7.40 (2H, d), 2.70-2.50 (1H, m), 2.65 (3H, s), 2.37-2.25 (1H, m), 2.10-2.00 (2H, m), 1.95-1.85 (2H, m), 1.65-1.40 (4H, m); MS 340.

Workup

  1. concentrationAfter 16 h the reaction mixture was concentrated in vacuo
  2. custompurified by reverse phase HPLC (150 mm×21 mm Phenomenex Column packed with Luna 10u C18 silica, eluting with 5-95% acetonitrile/water)

Sources & evidence

ORD record
ord-6c917c6ecd7e4efbbdd5220d5e34123d
Source dataset
uspto-grants-2011_08
Patent number
US07994179B2

Reaction notes

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