Sodium Hydroxide → 4-[1-(2,3-Difluoro-phenyl)-1H-tetrazol-5-yl]-1-methanesulfonyl-1H-pyrrole-2-carboxylic acid methyl ester

HRID 2249521Notes

Reaction equation

HRID 2249521 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([S:22]([CH3:25])(=[O:24])=[O:23])[CH:7]=[C:8]([C:10](=[N:20][NH2:21])[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=2[F:19])[CH:9]=1)=[O:4].[N:26]([O-])=O.[Na+].[OH-].[Na+]>Cl.O>[CH3:1][O:2][C:3]([C:5]1[N:6]([S:22]([CH3:25])(=[O:24])=[O:23])[CH:7]=[C:8]([C:10]2[N:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=3[F:19])[N:26]=[N:21][N:20]=2)[CH:9]=1)=[O:4]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 178498204HCID 178498204, compound

Product 1

HCID 596396944-[1-(2,3-Difluoro-phenyl)-1H-tetrazol-5-yl]-1-methanesulfonyl-1H-pyrrole-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 4-[N-(2,3-difluoro-phenyl)-N′-amino-carbamimidoyl]-1-methanesulfonyl-1H-pyrrole-2-carboxylic acid methyl ester (250 mg, 0.67 mmol) in 2N HCl (10 mL) was added a solution of NaNO2 (56 mg, 0.81 mmol) in water (2 mL) slowly at 0° C. The reaction mixture was stirred at this temperature for 5 minutes and then neutralized by addition of 6N NaOH. The resulting white precipitate was collected by filtration and washed with water. After drying on the vacuum pump for 6 hours, the crude product was obtained (250 mg, 97%) as white solid. 1H NMR (500 MHz, DMSO-d6) δ7.94 (q, 1H), 7.78 (t, 1H), 7.68 (s, 1H), 7.60 (q, 1H), 7.15 (s, 1H), 3.94 (s, 3H), 3.82 (s, 3H) ppm. MS (ES+): m/e=384.1 (M+H); LC/Method A/3.63 min.

Workup

  1. filtrationThe resulting white precipitate was collected by filtration
  2. washwashed with water
  3. customAfter drying on the vacuum pump for 6 hours

Sources & evidence

ORD record
ord-808ec1290a094122a5f4f0472ebc75a3
Source dataset
uspto-grants-2008_01
Patent number
US07314885B2

Reaction notes

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