Sodium Hydroxide → HCID 178514785, compound

HRID 69778Notes

Reaction equation

HRID 69778 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2C(=O)[O:12][N:11]=[C:10]2[C:15]2[C:16]([NH:20][CH2:21][CH2:22][NH:23][S:24]([NH2:27])(=[O:26])=[O:25])=[N:17][O:18][N:19]=2)[CH:5]=[CH:6][C:7]=1[F:8].[OH-].[Na+]>CO>[NH2:27][S:24]([NH:23][CH2:22][CH2:21][NH:20][C:16]1[C:15]([C:10](=[N:11][OH:12])[NH:9][C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=2)=[N:19][O:18][N:17]=1)(=[O:25])=[O:26]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66606394N-[2-({4-[4-(3-Chloro-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-yl}amino)ethyl]sulfamide

Product 1

HCID 178514785HCID 178514785, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of N-[2-({4-[4-(3-chloro-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-yl}amino)ethyl]sulfamide (3.7 g, 8.8 mmol) in methanol (70 mL) was treated with 2M NaOH (18 mL, 35 mmol) and stirred at 25° C. for 2 h. The reaction mixture was quenched with 6N HCl to pH˜7 and the methanol was removed under reduced pressure. The solid that precipitated was filtered and washed with water to give the desired product (3.2 g, 92%) as a white solid. LCMS for C11H14ClFN7O4S (M+H)+: m/z=394.0. 1H NMR (400 MHz, DMSO-d6): δ 7.96 (dd, J=6.8, 2.1 Hz, 0.05H), 7.32-7.29 (m, 0.1H), 7.18 (dd, J=9.1, 9.1 Hz, 0.95H), 6.93 (dd, J=6.4, 2.7 Hz, 0.95H), 6.71-6.66 (m, 0.95H), 6.33 (br s, 1 H), 3.35-3.27 (m, 2 H), 3.10-3.06 (m, 2 H).

Workup

  1. customThe reaction mixture was quenched with 6N HCl to pH˜7
  2. customthe methanol was removed under reduced pressure
  3. customThe solid that precipitated
  4. filtrationwas filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-a161615076184372bf7339b21d9c26e3
Source dataset
uspto-grants-2014_09
Patent number
US08822511B2

Reaction notes

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