Ethylenediamine → HCID 71254760, compound

HRID 540327Notes

Reaction equation

HRID 540327 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][N:10]([C:12]3[CH:21]=[C:20](Cl)[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]=3)[C:9](=[O:23])[CH2:8][CH2:7][C:6]=2[CH:24]=1.[CH2:25]([NH2:28])[CH2:26][NH2:27]>>[NH2:27][CH2:26][CH2:25][NH:28][C:20]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=[C:12]([N:10]2[C:9](=[O:23])[CH2:8][CH2:7][C:6]3[CH:24]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=3[CH2:11]2)[CH:21]=1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 71254491HCID 71254491, compound

Product 1

HCID 71254760HCID 71254760, compoundYield 98%

Conditions

Temperature
170 °C

Procedure

To a solution of 7-bromo-2-(4-chloroquinolin-2-yl)-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one (40 mg, 0.1 mmol) was added ethane-1,2-diamine (0.5 mL) in a microwave vessel, which was degassed and refilled with nitrogen. The resultant mixture was heated at 170° C. under microwave irradiation for 30 minutes. After cooled to room temperature, the mixture was diluted with methanol (10 mL) and concentrated under reduced pressure to give a residue which was purified by preparative HPLC to afford 42 mg of product as a solid (yield was 98%). MS obsd. (ESI+) [(M+H)+] 424. 1H NMR (400 MHz, CD3OD) δ ppm 7.99 (d, J=8.0 Hz, 1 H), 7.73 (d, J=8.0 Hz, 1 H), 7.58 (m, 2 H), 7.47 (s, 2 H), 7.32 (td, J=1.2, 8.8 Hz, 1 H), 6.04 (s, 1 H), 5.48 (s, 2 H), 3.42 (t, J=6.4 Hz, 2 H), 3.11 (t, J=7.6 Hz, 2 H), 2.98 (t, J=6.0 Hz, 2 H), 2.86 (t, J=7.2 Hz, 2 H).

Workup

  1. customwhich was degassed
  2. additionrefilled with nitrogen
  3. temperatureAfter cooled to room temperature
  4. additionthe mixture was diluted with methanol (10 mL)
  5. concentrationconcentrated under reduced pressure
  6. customto give a residue which
  7. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-601e947fb2b9415b96d4718a61643a8b
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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