Acetic Acid → HCID 58497435, compound

HRID 2175198Notes

Reaction equation

HRID 2175198 reaction equation
C[O:2][C:3](=[O:38])[CH2:4][C@@H:5]([N:13]1[C:17]2=[N:18][C:19]([C:22]#[N:23])=[CH:20][CH:21]=[C:16]2[N:15]([CH2:24][C:25]2[C:33]3[C:28](=[CH:29][C:30]([CH3:35])=[CH:31][C:32]=3[CH3:34])[N:27]([CH3:36])[CH:26]=2)[C:14]1=[O:37])[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.O.[OH-].[Li+].C(O)(=[O:44])C>O1CCOCC1.O>[C:22]([C:19]1[N:18]=[C:17]2[N:13]([C@@H:5]([C:6]3[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=3)[CH2:4][C:3]([OH:2])=[O:38])[C:14](=[O:37])[N:15]([CH2:24][C:25]3[C:33]4[C:28](=[CH:29][C:30]([CH3:35])=[CH:31][C:32]=4[CH3:34])[N:27]([CH3:36])[CH:26]=3)[C:16]2=[CH:21][CH:20]=1)(=[O:44])[NH2:23]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 168937Lithium hydroxide, monohydrateHCID 58497457HCID 58497457, compound

Product 1

HCID 58497435HCID 58497435, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of (R)-3-[5-cyano-2-oxo-1-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl]-3-(4-fluoro-phenyl)-propionic acid methyl ester (0.17 g, 0.33 mmol) in dioxane (10 ml) and water (3 ml) was added lithium hydroxide monohydrate (70 mg, 1.66 mmol). The reaction was stirred for 24 hours after which time it was diluted with water and acidified using acetic acid. The resulting precipitate was collected via filtration and washed with water. The remaining solid was purified via preparative TLC (2×1 mm silica gel plates, 5% MeOH/Dichloromethane) to afford 22 mg (13%) of the title compound. LCMS, M++1, m/z: 516.20.

Workup

  1. filtrationThe resulting precipitate was collected via filtration
  2. washwashed with water
  3. customThe remaining solid was purified via preparative TLC (2×1 mm silica gel plates, 5% MeOH/Dichloromethane)

Sources & evidence

ORD record
ord-68aafeb2e0fd4bee964285e012a7c953
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

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