Sodium Hydroxide → HCID 71090365, compound

HRID 331065Notes

Reaction equation

HRID 331065 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][C:3]=1[C:13]1[C:21]2[C:16](=[N:17][CH:18]=[CH:19][C:20]=2[NH:22][S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:25])=[O:24])[N:15]([CH3:32])[C:14]=1[C:33]([O:35]C)=[O:34].[OH-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][C:3]=1[C:13]1[C:21]2[C:16](=[N:17][CH:18]=[CH:19][C:20]=2[NH:22][S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:25])=[O:24])[N:15]([CH3:32])[C:14]=1[C:33]([OH:35])=[O:34]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71090395HCID 71090395, compound

Product 1

HCID 71090365HCID 71090365, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of methyl 3-(2-fluoro-5-(pyrrolidin-1-yl)phenyl)-1-methyl-4-(phenylsulfonamido)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate (47 mg, 0.092 mmol) in MeOH (1 mL) stirred under nitrogen at RT was added a aqueous solution of 6M sodium hydroxide (0.077 mL, 0.462 mmol) in one charge. The reaction mixture was stirred at 80° C. for 2 hours. The reaction mixture was cooled to RT and concentrated. The crude was purified on normal phase silica eluting with 2M ammonia in MeOH and DCM (0-50%) to give the title compound (35 mg). LCMS (A): m/z (M+H)+ 495, C25H23FN4O4S requires 494 (basic).

Workup

  1. additioncharge
  2. stirringThe reaction mixture was stirred at 80° C. for 2 hours
  3. temperatureThe reaction mixture was cooled to RT
  4. concentrationconcentrated
  5. customThe crude was purified on normal phase silica eluting with 2M ammonia in MeOH and DCM (0-50%)

Sources & evidence

ORD record
ord-ef94ea9fa7154935814f35b88b99fdcc
Source dataset
uspto-grants-2014_11
Patent number
US08877742B2

Reaction notes

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