(2-Chloro-4-methylphenyl)boronic acid → 2'-Chloro-4'-methyl-biphenyl-4-carboxylic acid {2-[(2-dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-amide

HRID 1175001Notes

Reaction equation

HRID 1175001 reaction equation
[CH3:1][N:2]([CH3:26])[CH2:3][CH2:4][N:5]([CH3:25])[C:6]1[S:7][C:8]2[CH:14]=[C:13]([NH:15][C:16](=[O:24])[C:17]3[CH:22]=[CH:21][C:20](I)=[CH:19][CH:18]=3)[CH:12]=[CH:11][C:9]=2[N:10]=1.[Cl:27][C:28]1[CH:33]=[C:32]([CH3:34])[CH:31]=[CH:30][C:29]=1B(O)O>>[ClH:27].[CH3:1][N:2]([CH3:26])[CH2:3][CH2:4][N:5]([CH3:25])[C:6]1[S:7][C:8]2[CH:14]=[C:13]([NH:15][C:16]([C:17]3[CH:22]=[CH:21][C:20]([C:29]4[CH:30]=[CH:31][C:32]([CH3:34])=[CH:33][C:28]=4[Cl:27])=[CH:19][CH:18]=3)=[O:24])[CH:12]=[CH:11][C:9]=2[N:10]=1.[CH3:1][N:2]([CH3:26])[CH2:3][CH2:4][N:5]([CH3:25])[C:6]1[S:7][C:8]2[CH:14]=[C:13]([NH:15][C:16]([C:17]3[CH:22]=[CH:21][C:20]([C:29]4[CH:30]=[CH:31][C:32]([CH3:34])=[CH:33][C:28]=4[Cl:27])=[CH:19][CH:18]=3)=[O:24])[CH:12]=[CH:11][C:9]=2[N:10]=1

Participants

4

Reactant 2

HCID 2773334(2-Chloro-4-methylphenyl)boronic acidHCID 57771748N-{2-[(2-dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-4-iodo-benzamide

Product 2

HCID 115474702'-Chloro-4'-methyl-biphenyl-4-carboxylic acid {2-[(2-dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-amideYield 1,320%HCID 693691612'-Chloro-4'-methyl-biphenyl-4-carboxylic acid {2-[(2-dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-amide hydrochloride salt

Procedure

The title compound is prepared by following a procedure analogous to Example 113, Step 1, using N-{2-[(2-dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-4-iodo-benzamide (0.40 g, 0.83 mmol) and 2-chloro-4-methyl-phenyl boronic acid (0.17 g, 0.10 mmol) to afford 2′-chloro-4′-methyl-biphenyl-4-carboxylic acid {2-[(2-dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-amide (0.21 g, 0.44 mmol, 53%). The material is dissolved in EtOH, treated with 1.0 M HCl in EtOH (0.44 mL), concentrated and recrystallized from EtOH/Heptane to give 0.20 g (88%) as the hydrochloride salt. LC/MS, Retention time=5.04 min; (m/z): calcd for C26H27ClN4OS (M+H)+: 479.4; found: 479.0.

Sources & evidence

ORD record
ord-a396dad10dbb47129c329c79a051696d
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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