Methacryloyl chloride → HCID 21963432, compound

HRID 2211922Notes

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](=[CH2:32])[C:29](Cl)=[O:30]>>[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:29](=[O:30])[C:28]([CH3:32])=[CH2:27])=[C:21]([CH3:26])[CH:20]=3)[CH2:15][CH2:16]2)=[N:3]1

Participants

Reactant 2

HCID 13528Methacryloyl chloride

HCID 21963230HCID 21963230, compound

Product 1

HCID 21963432HCID 21963432, compoundYield 73%

Procedure

Starting with 4-[2-(4-benzo[d]isothiazol-3-yl-piperazin-1-yl)-ethyl]-2-methyl-phenylamine hydrochloride (0.6 g, 1.702 mmol) and 2-methyl-acryloyl chloride (0.206 mL, 1.702 mmol) and following the procedure outlined in Example 512, N-{4-[2-(4-Benzo[d]isothiazol-3-yl-piperazin-1-yl)-ethyl]-2-methyl-phenyl}-2-methyl-acrylamide (0.521 g, 1.239 mmole) was obtained. Yield=73%. 100% purity at 254 nM; LCMS (APCI): 421.3 [M+H]+; 1H NMR (400 MHz, DMSO-d6) 811.17 (bs, 1H), 9.32 (s, 1H), 8.10 d, J=7.88 Hz, 1H), 8.07 (d, J=7.88 Hz, 1H), 7.55 (t, J=7.88 Hz, 1H), 7.43 (t, J=7.88 Hz, 1H), 7.19 (d, J=7.88 Hz, 1H), 7.11 (s, 1H), 7.05 (d, J=7.88 Hz, 1H), 5.80 (s, 1H), 5.44 (s, 1H), 4.05 (bd, J=12.08 Hz, 2H), 3.63 (bd, J=12.08 Hz, 2H), 3.51–3.32 (m, 5H), 3.31 (s, H2O), 3.29–3.22 (m, 1H), 3.07–2.98 (m, 2H), 2.12 (s, 3H), 1.90 (s, 3H).

Sources & evidence

ORD record: ord-94f00aa8517b44138ebfaefdd76dff56
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101886B2

Reaction notes

Loading…