Ethylenediamine → HCID 71262269, compound

HRID 540317Notes

Reaction equation

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

Participants

Reactant 2

HCID 3301Ethylenediamine

HCID 71255102HCID 71255102, compound

Product 1

HCID 71262269HCID 71262269, compoundYield 46.5%

Conditions

Temperature: 150 °C

Procedure

The mixture of 2-(4-chloroquinolin-2-yl)-7-(methylsulfonyl)-2,3,4,5-tetrahydro-1H-2-benzazepine (55.6 mg, 0.144 mmol) and ethane-1,2-diamine (1 mL) was heated with stirring in a 10 mL microwave process vial for 2 hours at 150° C. under microwave irradiation. The solvent was removed in vacuo and the residue was purified by preparative HPLC to give 27.5 mg of product as a light-yellow solid (yield was 46.5%). MS obsd. (ESI+) [(M+H)+] 411. 1H NMR (400 MHz, CD3OD) δ ppm 7.82-7.73 (m, 4 H), 7.53 (d, J=7.6 Hz, 1 H), 7.45-7.40 (m, 1 H), 7.12-7.08 (m, 1 H), 5.98 (s, 1 H), 4.96 (s, 2 H), 4.16 (s, 2 H), 3.41 (t, J=6.4 Hz, 2 H), 3.16 (brs, 2 H), 3.06 (s, 3 H), 2.97 (t, J=6.4 Hz, 2 H), 1.96 (brs, 2 H).

Workup

temperaturewas heated
customThe solvent was removed in vacuo
customthe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-38ec70909df847e28e47eea64d5f554e
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871756B2

Reaction notes

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