3-[4-(Trifluoromethyl)phenyl]prop-2-enoyl chloride → N-[2-(Isopropyl-methyl-amino)-benzothiazol-6-yl]-3-(4-trifluoromethyl-phenyl)-acrylamide

HRID 1174914Notes

Reaction equation

HRID 1174914 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9](Cl)=[O:10])=[CH:5][CH:4]=1.[CH:16]([N:19]([CH3:30])[C:20]1[S:21][C:22]2[CH:28]=[C:27]([NH2:29])[CH:26]=[CH:25][C:23]=2[N:24]=1)([CH3:18])[CH3:17]>>[CH:16]([N:19]([CH3:30])[C:20]1[S:21][C:22]2[CH:28]=[C:27]([NH:29][C:9](=[O:10])[CH:8]=[CH:7][C:6]3[CH:12]=[CH:13][C:3]([C:2]([F:15])([F:14])[F:1])=[CH:4][CH:5]=3)[CH:26]=[CH:25][C:23]=2[N:24]=1)([CH3:18])[CH3:17]

Participants

3

Reactant 2

HCID 542691863-[4-(Trifluoromethyl)phenyl]prop-2-enoyl chlorideHCID 57771707N2-Isopropyl-N2-methyl-benzothiazole-2,6-diamine

Product 1

HCID 68771374N-[2-(Isopropyl-methyl-amino)-benzothiazol-6-yl]-3-(4-trifluoromethyl-phenyl)-acrylamideYield 26%

Procedure

Prepare according to Method D (Example 17), using 4-trifluoromethylcinnamoyl chloride (526 mg, 2.24 mmol) (Example 17) and N2-isopropyl-N2-methyl-benzothiazole-2,6-diamine (332 mg, 1.50 mmol), to afford the title compound (163 mg, 26%). mass spectrum (m/e): 420.2 [M+H], 418.2 [M−H]. 1H NMR (400 MHz, DMSO-d6): δ 10.30 (s, 1H), 8.25 (d, 1H, J=1.8 Hz), 7.87-7.78 (m, 4H), 7.64 (d, 1H, J=15.8 Hz), 7.43 (dd, 1H, J=8.6, 1.9 Hz), 7.39 (d, 1H, J=8.4 Hz), 6.96 (d, 1H, J=15.4 Hz), 4.32 (m, 1H), 2.97 (s, 3H), 1.22 (d, 6H, J=7.0 Hz).

Workup

  1. customPrepare

Sources & evidence

ORD record
ord-5ead580d5e354b3cbda779bd01bf4a4a
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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