3-Methyl-2-butenoyl chloride → HCID 131725913, compound

HRID 2211924Notes

Reaction equation

HRID 2211924 reaction equation
Cl.[S:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([NH2:25])=[C:21]([CH3:26])[CH:20]=3)[CH2:13][CH2:12]2)=[N:3]1.[CH3:27][C:28]([CH3:33])=[CH:29][C:30](Cl)=[O:31]>>[S:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]([N:11]2[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:30](=[O:31])[CH:29]=[C:28]([CH3:33])[CH3:27])=[C:21]([CH3:26])[CH:20]=3)[CH2:15][CH2:16]2)=[N:3]1

Participants

3

Reactant 2

HCID 1023943-Methyl-2-butenoyl chlorideHCID 21963230HCID 21963230, compound

Product 1

HCID 131725913HCID 131725913, compoundYield 75%

Procedure

Starting with 4-[2-(4-benzo[d]isothiazol-3-yl-piperazin-1-yl)-ethyl]-2-methyl-phenylamine hydrochloride (0.60 g, 1.702 mmol) and 3,3-dimethyl-acryloyl chloride (0.189 mL, 1.702 mmol) and following the procedure outlined in Example 512, 3-methyl-but-2-enoic acid{4-[2-(4-benzo[d]isothiazol-3-yl-piperazin-1-yl)-ethyl]-2-methyl-phenyl]amide (0.553 g, 1.261 mmol) was obtained. Yield=75%. 100% purity at 254 nM; LCMS (APCI): 435.3 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 9.05 (s, 1H), 8.00 (d, J=8.42 Hz, 2H), 7.50 (t, J=7.47 Hz, 1H), 7.38 (t, J=7.47 Hz, 1H), 7.26 (d, J=7.47 Hz, 1H), 7.02 (s, 1H), 6.97 (d, J=7.47 Hz, 1H), 5.90 (s, 1H), 3.44–3.36 (m, 4H), 3.30 (s, H2O), 2.71–2.58 (m, 6H), 2.57–2.49 (m, 2H), 2.45 (p, DMSO), 2.11 (s, 3H), 2.07 (s, 3H), 1.80 (s, 3H).

Sources & evidence

ORD record
ord-9b675d5ba2e142eabb2c89fbfe640188
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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