Ethylenediamine → HCID 71255516, compound

HRID 540322Notes

Reaction equation

HRID 540322 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[CH:10]=2)[N:5]=[C:4]([N:19]2[CH2:25][CH2:24][CH2:23][C:22]3[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=3[CH2:20]2)[CH:3]=1.[CH2:30]([NH2:33])[CH2:31][NH2:32]>>[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[C:4]([N:19]1[CH2:25][CH2:24][CH2:23][C:22]3[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=3[CH2:20]1)[CH:3]=[C:2]2[NH:32][CH2:31][CH2:30][NH2:33]

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 71255048HCID 71255048, compound

Product 1

HCID 71255516HCID 71255516, compound

Conditions

Temperature
180 °C

Procedure

The mixture of 2-[4-chloro-6-(pyridin-2-yloxy)quinolin-2-yl]-2,3,4,5-tetrahydro-1H-2-benzazepine (40 mg, 0.1 mmol) and ethane-1,2-diamine (2 mL) was heated with stirring in a 5 mL microwave process vial for 3 hours at 180° C. under microwave irradiation. The solvent was removed under reduced pressure and the residue was purified by preparative HPLC to give 7 mg of product as a yellow powder. MS obsd. (ESI+) [(M+H)+] 426. 1H NMR (400 MHz, CD3OD) δ ppm 8.12 (d, J=3.2 Hz, 1 H), 7.82-7.78 (m, 1 H), 7.66 (d, J=2.8 Hz, 1 H), 7.61 (d, J=8.8 Hz, 1 H), 7.48 (d, J=6.8 Hz, 1 H), 7.23 (dd, J=5.2, 2.4 Hz, 1 H), 7.16-7.08 (m, 4 H), 6.90 (d, J=8.4 Hz, 1 H), 6.04 (s, 1 H), 4.83 (s, 2 H), 4.16 (brs, 2 H), 3.41 (t, J=6.2 Hz, 2 H), 3.05 (t, J=4.8 Hz, 2 H), 2.94 (t, J=6.2 Hz, 2 H), 1.96-1.91 (m, 2 H).

Workup

  1. temperaturewas heated
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-588d246236224433a3f9e601485c8ff0
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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