2,6-Dichlorobenzothiazole → 4-{4'-[(6-Chloro-1,3-benzothiazol-2-yl)amino]-1,1'-biphenyl-4-yl}-2-[2-(dimethylamino)ethyl]-4-oxobutanoic acid

HRID 9596

Reaction equation

HRID 9596 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:26])[CH2:15][CH:16]([CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])[C:17]([O:19]C)=[O:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl[C:28]1[S:29][C:30]2[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:31]=2[N:32]=1.S1C2C=CC=CC=2N=C1NC1C=CC(C2C=CC(C(=O)CC(C)(C)C(O)=O)=CC=2)=CC=1.FC(F)(F)C([O-])=O>>[Cl:37][C:35]1[CH:34]=[CH:33][C:31]2[N:32]=[C:28]([NH:1][C:2]3[CH:7]=[CH:6][C:5]([C:8]4[CH:13]=[CH:12][C:11]([C:14](=[O:26])[CH2:15][CH:16]([CH2:21][CH2:22][N:23]([CH3:24])[CH3:25])[C:17]([OH:19])=[O:18])=[CH:10][CH:9]=4)=[CH:4][CH:3]=3)[S:29][C:30]=2[CH:36]=1

Participants

5

Reactant 4

HCID 771762,6-DichlorobenzothiazoleHCID 84468TrifluoroacetateHCID 114759304-[4'-(1,3-Benzothiazol-2-ylamino)-1,1'-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoic acidHCID 21985852Methyl 4-(4'-amino-1,1'-biphenyl-4-yl)-2-[2-(dimethyl-amino)ethyl]4-oxobutanoate

Product 1

HCID 115552524-{4'-[(6-Chloro-1,3-benzothiazol-2-yl)amino]-1,1'-biphenyl-4-yl}-2-[2-(dimethylamino)ethyl]-4-oxobutanoic acidYield 16.3%

Procedure

This compound was prepared from methyl 4-(4′-amino-1,1′-biphenyl-4-yl)-2-[2-(dimethyl-amino)ethyl]-4-oxobutanoate (60 mg, 0.17 mmol) and 2,6-dichloro-1,3-benzothiazole (51.8 mg, 0.25 mmol)) in a similar manner to the method described for 4-[4′-(1,3-benzothiazol-2-ylamino)-1,1′-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoic acid, providing 14.1 mg (13%) of the desired product as the trifluoroacetate salt. 1H NMR (400 MHz, CD3OD) δ 8.10 (d, 2 H), 7.70–8.10 (m, 8 H), 7.30 (m, 1H), 3.60 (m, 1 H), 3.30–3.40 (m, 3 H), 3.10 (m, 1 H), 2.95 (s, 6 H), 2.20 (m, 1 H), 2.00 (m, 1 H). LC-MS m/z 508.1 (MH+), ret. time 2.66 min.

Sources & evidence

ORD record
ord-7c19388199054a7cbfef998edf07e7ca
Source dataset
uspto-grants-2006_08
Patent number
US07091228B2

Linked notes

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