(2-Benzoylamino-4-methoxy-benzothiazol-7-yl)-(4-methyl-benzyl)-carbamic acid 2,2,2-trichloro-ethyl ester → N-[4-methoxy-7-(4-methyl-benzylamino)-benzothiazol-2-yl]-benzamide

HRID 51865Notes

Reaction equation

ClC(Cl)(Cl)COC(=O)[N:6]([C:15]1[C:23]2[S:22][C:21]([NH:24][C:25](=[O:32])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:20][C:19]=2[C:18]([O:33][CH3:34])=[CH:17][CH:16]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1>C(O)(=O)C.[Zn]>[CH3:34][O:33][C:18]1[C:19]2[N:20]=[C:21]([NH:24][C:25](=[O:32])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[S:22][C:23]=2[C:15]([NH:6][CH2:7][C:8]2[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][CH:13]=2)=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 100 mg (01.17 mmol) (2-benzoylamino-4-methoxy-benzothiazol-7-yl)-(4-methyl-benzyl)-carbamic acid 2,2,2-trichloro-ethyl ester in 3 ml acetic acid at room temperature was added 90 mg (1.34 mmol) activated zinc powder and the mixture was heated at 80° C. for 16 hours. The mixture was then filtered and the filtrate concentrated in vacuo. Flash chromatography (ethyl acetate/hexane) afforded 15 mg (21%) N-[4-methoxy-7-(4-methyl-benzylamino)-benzothiazol-2-yl]-benzamide as a yellow crystalline solid, ES-MS m/e (%): 426 (M+Na+, 27), 404 (M+H+, 100), and 10 mg (13%) N-{7-[acetyl-(4-methyl-benzyl)-amino]-4-methoxy-benzothiazol-2-yl}-benzamide as a yellow crystalline solid, ES-MS m/e (%): 468 (M+Na+, 12), 446 (M+H+, 100).

Workup

filtrationThe mixture was then filtered
concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record: ord-0dfa46575f2b49228650894a4566bd8b
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713499B2

Reaction notes

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