Hydrochloric Acid → HCID 21069816, compound

HRID 1788129Notes

Reaction equation

HRID 1788129 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[S:12]([NH:15][CH3:16])(=[O:14])=[O:13])=[N+]=[N-].[ClH:17]>C(O)C.[Pd]>[ClH:17].[NH2:1][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[S:12]([NH:15][CH3:16])(=[O:13])=[O:14]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21069826HCID 21069826, compound

Product 1

HCID 21069816HCID 21069816, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of intermediate 51, 2-azidomethyl-5-fluoro-N-methyl-benzenesulfonamide, (560 mg, 2.3 mmol) in ethanol (10 mL) was added 6N HCl (1 mL) and 10% Pd—C (100 mg) and the mixture hydrogenated with 1 atm of H2 for 14 hrs. The catalyst was removed by filtration through Celite and the filtrate concentrated in vacuo to provide 630 mg (Yield >100%) of the title compound. 1H NMR (500 MHz, DMSO-D6) δ ppm: 4.36 (2 H, d, J=5.2 Hz) 7.63-7.70 (2 H, m) 7.77-7.83 (1 H, m) 8.11 (1 H, d, J=4.9 Hz) 8.41 (3 H, s); LC/MS m/z 219 (M+H).

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-2951742908a2472ab70fe369497278e0
Source dataset
uspto-grants-2009_03
Patent number
US07511037B2

Reaction notes

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