Methanol → HCID 117807853, compound

HRID 2206534Notes

Reaction equation

HRID 2206534 reaction equation
C([O:3][C:4](=[O:38])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([CH:12]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([C:23](=[O:36])[NH:24][CH2:25][C:26]3[C:27](=[O:35])[NH:28][C:29]([CH3:34])=[CH:30][C:31]=3[O:32][CH3:33])=[C:15]2[CH3:37])[CH3:13])[CH2:8][CH2:7]1)C.C1COCC1.CO.O.[OH-].[Li+]>O>[CH3:33][O:32][C:31]1[CH:30]=[C:29]([CH3:34])[NH:28][C:27](=[O:35])[C:26]=1[CH2:25][NH:24][C:23]([C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:14]([CH:12]([CH:9]2[CH2:8][CH2:7][N:6]([CH2:5][C:4]([OH:38])=[O:3])[CH2:11][CH2:10]2)[CH3:13])[C:15]=1[CH3:37])=[O:36]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 117807849HCID 117807849, compound2×

Product 1

HCID 117807853HCID 117807853, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a round bottomed flask was charged with a magnetic stir bar was added (R or S)-ethyl-2-(4-(1-(3-((4-methoxy-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methylcarbamoyl)-2-methyl-1H-indol-1-yl)ethyl)piperidin-1-yl)acetate (Compound 363) (69 mg, 0.132 mmol), THF (1.5 mL), MeOH (1.5 mL), and water (0.75 mL). To this solution was added lithium hydroxide monohydrate (5.54 mg, 0.132 mmol) and the reaction stirred at room temperature for 1H. The organics were removed under reduced pressure and the resulting aqueous solution purified via reverse phase-HPLC (water/MeCN) 0→95% to afford the title compound (66 mg, 0.108 mmol, 82% yield). LCMS 514 (M+1) 1H NMR (400 MHz, DMSO-d6) δ=11.67 (s, 1H), 9.65 (s, 1H), 7.84-7.68 (m, 2H), 7.63 (d, J=7.4 Hz, 1H), 7.14-7.03 (m, 2H), 6.18 (s, 1H), 4.33 (d, J=3.6 Hz, 2H), 4.27-4.15 (m, 1H), 4.04 (br. s., 2H), 3.85 (s, 3H), 3.57 (s, 1H), 3.35-3.23 (m, 1H), 3.14-2.99 (m, 1H), 2.86-2.74 (m, 1H), 2.62 (s, 3H), 2.21 (s, 3H), 2.18-2.08 (m, 1H), 1.75 (s, 1H), 1.60-1.49 (m, 4H), 1.46-1.33 (m, 1H), 0.92-0.81 (m, 1H).

Workup

  1. additionTo a round bottomed flask was charged with a magnetic stir bar
  2. customThe organics were removed under reduced pressure
  3. customthe resulting aqueous solution purified via reverse phase-HPLC (water/MeCN) 0→95%

Sources & evidence

ORD record
ord-70a7c70dd26d468e825b9609390f4c26
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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