Triethylamine → HCID 11706696, compound

HRID 916557Notes

Reaction equation

[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH:13]([NH:21][C:22](=[O:24])[CH3:23])[CH2:14][N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[CH:7][C:5]=2[N:6]=1.C(N(CC)CC)C.[CH:32]1[C:44]2[CH2:43][C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:36]=2[CH:35]=[CH:34][C:33]=1[N:45]=[C:46]=[O:47]>O1CCCC1>[CH:32]1[C:44]2[CH2:43][C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:36]=2[CH:35]=[CH:34][C:33]=1[NH:45][C:46]([N:18]1[CH2:17][CH2:16][N:15]([CH2:14][CH:13]([NH:21][C:22](=[O:24])[CH3:23])[CH2:12][O:11][C:8]2[CH:9]=[CH:10][C:4]3[S:3][C:2]([CH3:1])=[N:6][C:5]=3[CH:7]=2)[CH2:20][CH2:19]1)=[O:47]

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of N-[2-(2-methylbenzothiazol-5-yloxy)-1-(piperazinylmethyl)ethyl]-acetamide (18.4 mg) in tetrahydrofuran (1 ml) was added triethylamine (25.6 μl) and 2-fluorenyl isocyanate (9.5 mg). The reaction mixture was stirred at 55° C. for 4 hours, producing a white precipitate. The precipitate was filtered off, and solvent removed from the filtrate under reduced pressure. The residue was purified by thin layer chromatography, developing with 4% methanol/methylene chloride, to provide N-{2-[4-(N-fluoren-2-ylcarbamoyl)piperazinyl]-1-[(2-methylbenzothiazol-5-yloxy)methyl]ethyl}acetamide (11.2 mg), a compound of Formula I.

Workup

customproducing a white precipitate
filtrationThe precipitate was filtered off
customsolvent removed from the filtrate under reduced pressure
customThe residue was purified by thin layer chromatography

Sources & evidence

ORD record: ord-8389fc75d6384b40b876baaf3954c84a
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271169B2

Reaction notes

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