Periodate → 1-(6-{[6-(4-Fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-1,3-benzothiazol-2-yl)-3-[2-(4-oxidomorpholin-4-yl)ethyl]urea

HRID 1035777Notes

Reaction equation

HRID 1035777 reaction equation
I([O-])(=O)(=O)=O.[Na].[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:20]([S:23][C:24]4[CH:44]=[CH:43][C:27]5[N:28]=[C:29]([NH:31][C:32]([NH:34][CH2:35][CH2:36][N:37]6[CH2:42][CH2:41][O:40][CH2:39][CH2:38]6)=[O:33])[S:30][C:26]=5[CH:25]=4)=[N:21][N:22]=3)[N:19]=2)=[CH:10][CH:9]=1.I([O-])(=O)(=O)=[O:46].[Na+]>O.C(O)(=O)C>[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:20]([S:23][C:24]4[CH:44]=[CH:43][C:27]5[N:28]=[C:29]([NH:31][C:32]([NH:34][CH2:35][CH2:36][N+:37]6([O-:46])[CH2:42][CH2:41][O:40][CH2:39][CH2:38]6)=[O:33])[S:30][C:26]=5[CH:25]=4)=[N:21][N:22]=3)[N:19]=2)=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 167232PeriodateHCID 5360545SodiumHCID 23667635Sodium periodateHCID 25182860Sar-125844

Product 1

HCID 867620901-(6-{[6-(4-Fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-1,3-benzothiazol-2-yl)-3-[2-(4-oxidomorpholin-4-yl)ethyl]ureaYield 75.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

116 mg of periodate of sodium in 0.5 cm3 of water are added to a mixture of 200 mg of 1-(6-{[6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-1,3-benzothiazol-2-yl)-3-[2-(morpholin-4-yl)ethyl]urea in 5 cm3 of acetic acid at 20° C. After an overnight period, the precipitate is filtered off. The white powder obtained is a mixture containing oxidized product and starting product. This mixture is taken up in 10 cm3 of acetic acid with 155 mg of sodium periodate dissolved in 1 cm3 of water. The mixture is left to stir overnight at 20° C. The precipitate is then filtered off and then washed successively with diisopropyl ether and with diethyl ether. 155 mg of white powder of 1-(6-{[6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-1,3-benzothiazol-2-yl)-3-[2-(4-oxidomorpholin-4-yl)ethyl]urea are obtained, the characteristics of which are as follows:

Workup

  1. filtrationthe precipitate is filtered off
  2. customThe white powder obtained
  3. additioncontaining oxidized product
  4. waitThe mixture is left
  5. filtrationThe precipitate is then filtered off
  6. washwashed successively with diisopropyl ether and with diethyl ether

Sources & evidence

ORD record
ord-9c9d0ad901df40f195f65aec9915434c
Source dataset
uspto-grants-2013_10
Patent number
US08546393B2

Reaction notes

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