2-Bromo-6-methoxy-1,3-benzothiazole → HCID 57553407, compound

HRID 1698061Notes

Reaction equation

C(OC([C:6]1[CH:33]=[CH:32][C:9]2[N:10]=[C:11]([C:13]3[CH:14]=[N:15][C:16]([N:19]4[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]4)=[CH:17][CH:18]=3)[S:12][C:8]=2[CH:7]=1)=O)C.BrC1SC2C=[C:42]([O:44]C)C=CC=2N=1>>[CH3:42][O:44][C:6]1[CH:33]=[CH:32][C:9]2[N:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([N:19]4[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]4)=[N:15][CH:14]=3)[S:12][C:8]=2[CH:7]=1

Participants

Reactant 2

HCID 112187652-Bromo-6-methoxy-1,3-benzothiazole

HCID 57553392HCID 57553392, compound

Product 1

HCID 57553407HCID 57553407, compound

Procedure

Tert-butyl 4-[5-(6-Methoxy-1,3-benzothiazol-2-yl)pyridin-2-yl]piperazine-1-carboxylate was prepared according to the method used for the preparation of 2-[6-[4-[(1,1-dimethylethoxy)carbonyl]-1-piperazinyl]-3-pyridinyl]-6-benzothiazolecarboxylic acid ethyl ester, from 2-bromo-6-methoxybenzothiazole (Yang et al. J. Biological Chem. 1989, 2, 891-898) (0.20 g), and obtained as a solid (0.23 g). 1H NMR δ 8.74 (s, 1H) 8.12 (d, 1H) 7.87 (d, 1H) 7.67 (s, 1H) 7.09 (dd, 1H) 6.98 (d, 1H) 3.84 (s, 3H) 3.64 (br. s., 4H) 3.45 (br. s., 4H) 1.43 (s, 9H); MS m/z M+H 427.

Sources & evidence

ORD record: ord-fe114e26c9e24ebba100e00f1d4d72c8
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163928B2

Reaction notes

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