Hydrochloric Acid → HCID 131725902, compound

HRID 10710Notes

Reaction equation

HRID 10710 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[CH:7][C:6]([CH:14]=[CH:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[O:17])=[C:5]([O:28][CH2:29][CH2:30][N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)[CH:4]=1.[ClH:37]>O1CCCC1>[ClH:37].[CH3:1][O:2][C:3]1[C:8]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[CH:7][C:6](/[CH:14]=[CH:15]/[C:16]([C:18]2[CH:19]=[CH:20][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:22][CH:23]=2)=[O:17])=[C:5]([O:28][CH2:29][CH2:30][N:31]2[CH2:32][CH2:33][O:34][CH2:35][CH2:36]2)[CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69645825HCID 69645825, compound

Product 1

HCID 131725902HCID 131725902, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Th 4-{3-[4-Methoxy-2-(2-morpholin-4-yl-ethoxy)-5-thiophen-2-yl-phenyl]-acryloyl}-benzenesulfonamide (Ex-81, 0.065 g, 0.12 mmol) was dissolved in tetrahydrofuran (5 mL) and 3 N HCl (1 mL) was added drop wise to the solution. The resulting yellow slurry was stirred in the dark at room temperature for 30 min. The precipitate was collected and dried in vacuo to yield 0.054 g (78%) of the title compound as a yellow solid, mp 235° C. (dec). 1H-NMR (300 MHz, DMSO-d6): δ 8.31–8.34 (m, 3H), 8.13 (d, 1H, J=15.0 Hz), 7.92–8.01 (m, 3H), 7.70 (d, 1H, J=4.0 Hz), 7.54 (m, 3H), 7.15–7.17 (m, 1H), 6.92 (s, 1H), 4.64 (brs, 2H), 4.03 (s, 5H), 3.72–3.79 (m, 4H), 3.56–3.60 (m, 4H). MS (ESI) m/z=529 ([M+H]+, 100%). Anal. Calcd. for C26H29ClN2O6S2: C, 55.26; H, 5.17; Cl, 6.27; N, 4.96; S, 11.35. Found: C, 55.31; H, 5.17; Cl, 6.32; N, 4.98; S, 11.20.

Workup

  1. customThe precipitate was collected
  2. customdried in vacuo

Sources & evidence

ORD record
ord-b854c4cccb7741fb8036de2735ec3c46
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Reaction notes

Loading…