Oxalyl chloride → 5-(4-Chloro-phenyl)-isoxazole-3-carboxylic acid [2-(isopropyl-methyl-amino)-benzothiazol-6-yl]-amide

HRID 1174913Notes

Reaction equation

HRID 1174913 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([C:13]([OH:15])=O)[CH:9]=2)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH:22]([N:25]([CH3:36])[C:26]1[S:27][C:28]2[CH:34]=[C:33]([NH2:35])[CH:32]=[CH:31][C:29]=2[N:30]=1)([CH3:24])[CH3:23]>>[CH:22]([N:25]([CH3:36])[C:26]1[S:27][C:28]2[CH:34]=[C:33]([NH:35][C:13]([C:10]3[CH:9]=[C:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)[O:12][N:11]=3)=[O:15])[CH:32]=[CH:31][C:29]=2[N:30]=1)([CH3:24])[CH3:23]

Participants

4

Reactant 3

HCID 65578Oxalyl chlorideHCID 11336445-(4-Chlorophenyl)isoxazole-3-carboxylic acidHCID 57771707N2-Isopropyl-N2-methyl-benzothiazole-2,6-diamine

Product 1

HCID 577717155-(4-Chloro-phenyl)-isoxazole-3-carboxylic acid [2-(isopropyl-methyl-amino)-benzothiazol-6-yl]-amideYield 36.2%

Procedure

Prepare according to Method C (Example 9), using 5-(4-chlorophenyl)isoxazole-3-carboxylic acid (39 mg, 0.174 mmol), oxalyl chloride (300 μL, 3.44 mmol), and N2-isopropyl-N2-methyl-benzothiazole-2,6-diamine (33 mg, 0.149 mmol) to afford the title compound (23 mg, 36%). mass spectrum (m/e): 427.0 [M+H]. 1H NMR (400 MHz, DMSO-d6) δ 10.76 (s, 1H), 8.24 (d, 1H, J=2.2 Hz), 8.01 (d, 2H, J=8.8 Hz), 7.66 (d, 2H, J=8.4 Hz), 7.60 (dd, 1H, J=8.8, 2.2 Hz), 7.54 (s, 1H), 7.41 (d, 1H, J=8.4 Hz), 4.34 (m, 1H), 2.98 (s, 3H), 1.23 (d, 6H, J=6.6 Hz).

Workup

  1. customPrepare

Sources & evidence

ORD record
ord-142475d182324d42a235841be06cd384
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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