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 517810Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([S:17][C:18]4[CH:36]=[CH:35][C:21]5[N:22]=[C:23]([NH:25][C:26](=[O:34])[O:27][C:28]6C=C[CH:31]=[CH:30][CH:29]=6)[S:24][C:20]=5[CH:19]=4)=[N:15][N:16]=3)[N:13]=2)=[CH:4][CH:3]=1.[OH:37]CC1CCO1.C(N(CC)CC)C>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([S:17][C:18]4[CH:36]=[CH:35][C:21]5[N:22]=[C:23]([NH:25][C:26](=[O:34])[O:27][CH2:28][CH:29]6[CH2:30][CH2:31][O:37]6)[S:24][C:20]=5[CH:19]=4)=[N:15][N:16]=3)[N:13]=2)=[CH:4][CH:3]=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-cff1f3b1216b45c0a7642409e8bd602d
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115134B2

Reaction notes

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