Methylamine → 4-(2-(Benzo[c][1,2,5]thiadiazol-5-yl)-1-(4-(2-(methylamino)-ethoxy)phenyl)but-1-enyl)phenol

HRID 626238Notes

Reaction equation

[N:1]1[S:2][N:3]=[C:4]2[CH:9]=[C:8]([C:10]([CH2:29][CH3:30])=[C:11]([C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)[C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20]Cl)=[CH:14][CH:13]=3)[CH:7]=[CH:6][C:5]=12.[CH3:31][NH2:32]>CO>[N:1]1[S:2][N:3]=[C:4]2[CH:9]=[C:8]([C:10]([CH2:29][CH3:30])=[C:11]([C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)[C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][NH:32][CH3:31])=[CH:14][CH:13]=3)[CH:7]=[CH:6][C:5]=12

Participants

Conditions

Temperature: 85 °C

Procedure

To a stirred solution of 4-(2-(benzo[c][1,2,5]thiadiazol-5-yl)-1-(4-(2-chloro-ethoxy)phenyl)but-1-enyl)phenol (83 mg) in 10 mL MeOH was added 3 mL CH3NH2 (30% aq.) and heated at 85° C. for 15 h. The organic solvent was removed in vacuo, and the remaining mixture was extracted with EtOAc. The extract was washed with water and brine, dried over Na2SO4, filtered, concentrated, and purified by column chromatography (CH2Cl2/MeOH(NH3 gas)=50/1) to give the desired product (11 mg, Z/E=1/1) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.81 (s, 1H), 7.68 (d, J=9.2 Hz, 1H), 7.15 & 7.06 (d, J=8.4 Hz, 2H), 6.86 (d, J=8.8 Hz, 1H), 6.79 (d, J=8.4 Hz, 2H), 6.78 & 6.72 (d, J=8.6 Hz, 2H), 6.48 & 6.42 (d, J=8.6 Hz, 2H), 4.12 & 3.92 (t, J=4.8 Hz, 2H), 3.03 & 2.91 (t, J=4.8 Hz, 2H), 2.60 (q, J=7.2 Hz, 2H), 2.55 & 2.47 (s, 3H), 0.97 (t, J=7.2 Hz, 3H); m/z=432[M+1]+.

Workup

customThe organic solvent was removed in vacuo
extractionthe remaining mixture was extracted with EtOAc
washThe extract was washed with water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
custompurified by column chromatography (CH2Cl2/MeOH(NH3 gas)=50/1)

Sources & evidence

ORD record: ord-91607c8956c14d1db85dec15771489ea
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309211B2

Reaction notes

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