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

HRID 9594Notes

Reaction equation

HRID 9594 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:24])[CH2:15][CH:16]([CH2:21][CH2:22][CH3:23])[C:17]([O:19]C)=[O:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl[C:26]1[S:27][C:28]2[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:29]=2[N:30]=1.S1C2C=CC=CC=2N=C1NC1C=CC(C2C=CC(C(=O)CC(C)(C)C(O)=O)=CC=2)=CC=1>>[Cl:35][C:33]1[CH:32]=[CH:31][C:29]2[N:30]=[C:26]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([C:8]4[CH:13]=[CH:12][C:11]([C:14](=[O:24])[CH2:15][CH:16]([CH2:21][CH2:22][CH3:23])[C:17]([OH:19])=[O:18])=[CH:10][CH:9]=4)=[CH:6][CH:7]=3)[S:27][C:28]=2[CH:34]=1

Participants

4

Reactant 3

HCID 771762,6-DichlorobenzothiazoleHCID 114759304-[4'-(1,3-Benzothiazol-2-ylamino)-1,1'-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoic acidHCID 21985717Methyl 2-[2-(4'-amino-1,1'-biphenyl-4-yl)-2-oxoethyl]-pentanoate

Product 1

HCID 117126972-(2-{4'-[(6-Chloro-1,3-benzothiazol-2-yl)amino]-1,1'-biphenyl-4-yl}-2-oxoethyl)pentanoic acidYield 18%

Procedure

This compound was prepared from methyl 2-[2-(4′-amino-1,1′-biphenyl-4-yl)-2-oxoethyl]-pentanoate (68 mg, 0.20 mmol) and 2,6-dichloro-1,3-benzothiazole (61.3 mg, 0.30 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 17.2 mg (18%) of the desired product. 1H NMR (400 MHz, DMSO-d6) δ 12.10 (br s, 1 H), 10.75 (br s, 1 H), 7.75–8.05 (m, 9 H), 7.60 (d, 1 H), 7.35 (m, 1 H), 3.40 (q, 1 H), 3.10 (m, 1 H), 1.55 (m, 2 H), 1.35 (m, 2 H), 0.85 (t, 3 H). LC-MS m/z 479.3 (MH+), ret. time 3.88 min.

Sources & evidence

ORD record
ord-b6d87980c92542e9aff42fd72cfa5451
Source dataset
uspto-grants-2006_08
Patent number
US07091228B2

Reaction notes

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