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

HRID 1174991Notes

Reaction equation

HRID 1174991 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]([Cl:34])[CH:31]=[CH:30][C:29]=1B(O)O>>[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:31]4[CH:30]=[CH:29][C:28]([Cl:27])=[CH:33][C:32]=4[Cl:34])=[CH:19][CH:18]=3)=[O:24])[CH:12]=[CH:11][C:9]=2[N:10]=1

Participants

3

Reactant 2

HCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 57771748N-{2-[(2-dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-4-iodo-benzamide

Product 1

HCID 115116562',4'-Dichloro-biphenyl-4-carboxylic acid {2-[(2-dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-amideYield 43%

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 (0.15 g, 0.31 mmol) and 2,4-dichloro-phenyl boronic acid (0.072 g, 0.38 mmol) to give the title compound (0.067 g, 0.13 mmol, 43%). LC/MS, Retention time=5.15 min; (m/z): calcd for C25H24Cl2N4OS: 499.5; found: 499.0.

Workup

  1. customThe title compound is prepared

Sources & evidence

ORD record
ord-e1b5648c5a1149609fd0905c99f60fbe
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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