Hydroxylamine → HCID 15957048, compound

HRID 2377053Notes

Reaction equation

HRID 2377053 reaction equation
[F:1][C:2]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:3]=1[CH2:4][N:5]1[C:9]2=[CH:10][N:11]=[C:12]([C:14]([O:16]C)=O)[CH:13]=[C:8]2[C:7]([CH2:18][N:19]2[CH2:24][CH2:23][C@@H:22]3[C:25](=[O:28])[NH:26][CH2:27][C@@H:21]3[CH2:20]2)=[CH:6]1.[OH-:34].[Na+].[NH2:36]O>CO>[F:1][C:2]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:3]=1[CH2:4][N:5]1[C:9]2=[CH:10][N:11]=[C:12]([C:14]([NH:36][OH:34])=[O:16])[CH:13]=[C:8]2[C:7]([CH2:18][N:19]2[CH2:24][CH2:23][C@@H:22]3[C:25](=[O:28])[NH:26][CH2:27][C@@H:21]3[CH2:20]2)=[CH:6]1

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 69198057HCID 69198057, compound

Product 1

HCID 15957048HCID 15957048, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of rac-methyl 1-(2,4-difluorobenzyl)-3-{[(3aR*,7aS*)-1-oxooctahydro-5H-pyrrolo[3,4-c]pyridin-5-yl]methyl}-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (0.09 g, 0.198 mmol) in MeOH (5 ml) was added 10% NaOH(aq) (0.5 ml, excess) and H2NOH (1 ml, excess, 50% wt. sol. in water). The resulting mixture was stirred for 16 hours at ambient temperature. The solvent was evaporated and the crude product was purified by reverse phase Prep-HPLC (20-60% acetonitrile:water) to provide the title compound as a white solid (0.032 g, 35%). 1H NMR (MeOH-d4) δ: 8.77 (s, 1H), 8.38 (s, 1H), 7.68 (s, 1H), 7.29-7.25 (m, 1H), 7.03-7.00 (m, 1H), 6.94-6.92 (m, 1H), 5.57 (s, 2H), 3.95-3.93 (m, 2H), 3.44-3.41 (m, H), 3.27-3.25 (m, 1H), 2.99-2.95 (m, 1H), 2.95-2.89 (m, 1H), 2.56-2.52 (m, 2H), 2.50-2.46 (m, 1H), 2.46-2.35 (m, H), 1.84-1.82 (m, H), 1.63-1.62 (m, H). LCMS (APCI, M+H+): 456.15. HPLC: 99% purity.

Workup

  1. customThe solvent was evaporated
  2. customthe crude product was purified by reverse phase Prep-HPLC (20-60% acetonitrile:water)

Sources & evidence

ORD record
ord-623544fe5500461eae74701c33288883
Source dataset
uspto-grants-2008_12
Patent number
US07468375B2

Reaction notes

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