Triethylamine → Oxetan-2-ylmethyl (6-{[6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-1,3-benzothiazol-2-yl)carbamate

HRID 1035772Notes

Reaction equation

[C:1]1([O:7][C:8](=[O:36])[NH:9][C:10]2[S:11][C:12]3[CH:18]=[C:17]([S:19][C:20]4[N:24]5[N:25]=[C:26]([C:29]6[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=6)[CH:27]=[CH:28][C:23]5=[N:22][N:21]=4)[CH:16]=[CH:15][C:13]=3[N:14]=2)C=C[CH:4]=[CH:3][CH:2]=1.[OH:37]CC1CCO1.C(N(CC)CC)C>O1CCCC1>[O:37]1[CH2:4][CH2:3][CH:2]1[CH2:1][O:7][C:8](=[O:36])[NH:9][C:10]1[S:11][C:12]2[CH:18]=[C:17]([S:19][C:20]3[N:24]4[N:25]=[C:26]([C:29]5[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=5)[CH:27]=[CH:28][C:23]4=[N:22][N:21]=3)[CH:16]=[CH:15][C:13]=2[N:14]=1

Participants

Conditions

Temperature: 80 °C

Procedure

a mixture of 171 mg of phenyl(6-{[6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-1,3-benzothiazol-2-yl)carbamate, 0.04 cm3 of 2-hydroxymethyloxetane and 0.06 cm3 of triethylamine in 3 cm3 of tetrahydrofuran is heated for 7.5 h in a bath at 80° C. The reaction is left to stand overnight at 20° C. and then the mixture is evaporated to dryness under vacuum. The residue is purified by chromatography on a Merck cartridge of 25 g of silica 15-40 μm by solid deposit, elution being carried out with a dichloromethane/methanol gradient of 100/0 to 96/04. 52 mg of oxetan-2-ylmethyl(6-{[6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-1,3-benzothiazol-2-yl)carbamate are thus obtained in the form of a white solid, the characteristics of which are as follows:

Workup

waitThe reaction is left
customthe mixture is evaporated to dryness under vacuum
customThe residue is purified by chromatography on a Merck cartridge of 25 g of silica 15-40 μm by solid deposit, elution

Sources & evidence

ORD record: ord-22c81ee882c3416fb834a44e97c0602e
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546393B2

Reaction notes

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