Methanol → HCID 67225063, compound

HRID 1968201Notes

Reaction equation

HRID 1968201 reaction equation
[O:1]=[C:2]([N:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)[C@H:3]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]2[N:14](C(OC(C)(C)C)=O)[CH:15]=[C:16]([C:17]([O:19]C)=[O:18])[C:9]=12)[CH2:4][CH3:5].CO.[OH-].[Na+]>C1COCC1>[O:1]=[C:2]([N:28]1[CH2:29][CH2:30][CH2:31][CH2:32]1)[C@H:3]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]2[NH:14][CH:15]=[C:16]([C:17]([OH:19])=[O:18])[C:9]=12)[CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 582935221H-Pyrrolo[2,3-b]pyridine-1,3-dicarboxylic acid, 4-[[[(1R)-1-(1-pyrrolidinylcarbonyl)propyl]amino]methyl]-, 1-(1,1-dimethylethyl) 3-methyl ester

Product 1

HCID 67225063HCID 67225063, compoundYield 7.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
53 °C

Procedure

To a 20 mL round bottom flask with a stirrer was added (R)-1-tert-butyl 3-methyl 4-((1-oxo-1-(pyrrolidin-1-yl)butan-2-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylate (150 mg, 0.337 mmol), MeOH (1 mL) and THF (1 mL). Aqueous NaOH (12 N, 1 mL) was added and the reaction mixture was stirred at 53° C. for 16 h. The solvent was removed and the resulting residue was further purified via preparative mass trigger LC-MS (AcCN/H2O, 5-50%). The fractions were collected, concentrated, and dried in vacuo to afford the title compound as a yellow oil (8.7 mg, 0.026 mmol, 7.80%). [M+H] calc'd for C17H22N4O3, 331; found, 331.6.

Workup

  1. customThe solvent was removed
  2. customthe resulting residue was further purified via preparative mass trigger LC-MS (AcCN/H2O, 5-50%)
  3. customThe fractions were collected
  4. concentrationconcentrated
  5. customdried in vacuo

Sources & evidence

ORD record
ord-4266642c4c6e44b4a6ebb827b6d5e8c9
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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