Pyridine → HCID 178514779, compound

HRID 1845783Notes

Reaction equation

HRID 1845783 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH2:9][CH2:10][C:11]1[C:12]([C:16]2[N:20]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[C:23]([Cl:28])[CH:22]=3)C(=O)[O:18][N:17]=2)=[N:13][O:14][N:15]=1.[S:30](N)([NH2:33])(=[O:32])=[O:31].N1C=CC=CC=1.[OH-].[Na+]>C(O)(=O)C>[Cl:28][C:23]1[CH:22]=[C:21]([NH:20][C:16]([C:12]2[C:11]([CH2:10][CH2:9][NH:8][S:30](=[O:32])(=[O:31])[NH2:33])=[N:15][O:14][N:13]=2)=[N:17][OH:18])[CH:26]=[CH:25][C:24]=1[F:27]

Participants

6

Reactant 4

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 82267SulfamideHCID 69268230HCID 69268230, compound

Product 1

HCID 178514779HCID 178514779, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-[4-(2-aminoethyl)-1,2,5-oxadiazol-3-yl]-4-(3-chloro-4-fluorophenyl)-1,2,4-oxadiazol-5(4h)-one trifluoroacetate (23.0 mg, 53.0 mmol), sulfamide (15.0 mg, 160 mmol) and pyridine (1.0 mL) was heated at 120° C. for 3 min in a microwave. To the reaction solution was added 0.5 mL 1 N NaOH and stirred for 30 min. The reaction solution was then acidified with acetic acid and purified by preparative LCMS to give the desired product (12 mg, 46%). MF=C11H12ClFN6O4S; LCMS calculated for C11H13ClFN6O4S (M+H)+: m/z=379.0. 1H NMR (400 MHz, DMSO-d6): d 11.52 (s, 1 H), 10.45 (s, 0.1 H), 9.05 (s, 0.1 H), 8.98 (s, 1 H), 7.95 (m, 0.1 H), 7.32 (m, 0.2 H), 7.15 (t, J=9.0 Hz, 1 H), 7.00 (dd, J=6.5 Hz, 2.7 Hz, 1 H), 6.76 (t, J=5.9 Hz, 1 H), 6.65 (m, 1 H), 6.59 (s, 2H), 3.29 (m, 2 H), 3.07 (t, J=7.2 Hz, 2 H);

Workup

  1. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-0be20c4508b44ca0ad0d6e38794978df
Source dataset
uspto-grants-2015_02
Patent number
US08951536B2

Reaction notes

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