Trifluoroacetic acid → HCID 25182856, compound

HRID 517794Notes

Reaction equation

FC(F)(F)C(O)=O.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:19]([C:21]([S:24][C:25]4[CH:41]=[CH:40][C:28]5[N:29]=[C:30]([NH:32]C(=O)OC(C)(C)C)[S:31][C:27]=5[CH:26]=4)=[N:22][N:23]=3)[N:20]=2)=[CH:11][CH:10]=1>ClCCl>[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:19]([C:21]([S:24][C:25]4[CH:41]=[CH:40][C:28]5[N:29]=[C:30]([NH2:32])[S:31][C:27]=5[CH:26]=4)=[N:22][N:23]=3)[N:20]=2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 20 °C

Procedure

4×0.1 cm3 of trifluoroacetic acid (containing 10% of anisole) are added to a mixture of 127 mg of 1,1-dimethylethyl (6-{[6-(4-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-1,3-benzothiazol-2-yl)carbamate in 5 cm3 of dichloromethane stirred at 20° C., this addition taking place over 7 h, until the starting product has disappeared. The reaction mixture is then concentrated under reduced pressure, so as to recover 186.5 mg of yellow powder which is purified by chromatography on Biotage Quad 12/25 (KP-SIL, 60 A; 32-63 μm), elution being carried out with a gradient of dichloromethane then dichloromethane/methanol: 99.5/0.5, 99/1, 98.5/1.5, 98/2, 97.5/2.5, 97/3. 36.6 mg of 6-{[6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-1,3-benzothiazol-2-amine are thus obtained in the form of a whitish powder, the characteristics of which are as follows:

Workup

additionthis addition
customover 7 h
concentrationThe reaction mixture is then concentrated under reduced pressure
customso as to recover 186.5 mg of yellow powder which
customis purified by chromatography on Biotage Quad 12/25 (KP-SIL, 60 A
wash32-63 μm), elution

Sources & evidence

ORD record: ord-cf39a931beba41fa95f1ed30e0aa62f6
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115134B2

Reaction notes

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