Acryloyl chloride → HCID 21963468, compound

HRID 2211921Notes

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

Participants

Reactant 2

HCID 13140Acryloyl chloride

HCID 21963230HCID 21963230, compound

Product 1

HCID 21963468HCID 21963468, compoundYield 74%

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 acryloyl chloride (0.138 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}-acrylamide (0.512 g, 1.259 mmol) was obtained. Yield=74%. 100% purity at 254 nM; LCMS (APCI): 407.3 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 11.02 (bs, 1H), 9.50 (s, 1H), 8.11 (d, J=8.22 Hz, 1H), 8.07 (d, J=8.22 Hz, 1H), 7.55 (t, J=7.3 Hz, 1H), 7.45–7.37 (m, 2H), 7.11 (s, 1H), 7.05 (d, 7.63 Hz, 1H), 6.50 (dd, J=10.09, J=17.08, 1H), 6.18 (dd, J=2.13 Hz, J=17.08 Hz, 1H), 5.69 (dd, J=2.05 Hz, J=10.05 hz, 1H), 4.10–4.00 (m, 2H), 3.70–3.59 (m, 2H), 3.50–3.33 (m, 4H), 3.29–3.21 (m, 1H), 3.07–2.95 (m, 2H), 2.16 (s, 3H).

Sources & evidence

ORD record: ord-56813bc5f53346f3b034e4b91ec0dbe3
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101886B2

Reaction notes

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