Ethylenediamine → HCID 71255083, compound

HRID 540325Notes

Reaction equation

HRID 540325 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[N:5]=[C:4]([N:13]2[CH2:19][CH2:18][CH2:17][C:16]3[CH:20]=[C:21]([C:24]([N:26]([CH3:28])[CH3:27])=[O:25])[CH:22]=[CH:23][C:15]=3[CH2:14]2)[CH:3]=1.[CH2:29]([NH2:32])[CH2:30][NH2:31]>>[NH2:31][CH2:30][CH2:29][NH:32][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[N:5]=[C:4]([N:13]2[CH2:19][CH2:18][CH2:17][C:16]3[CH:20]=[C:21]([C:24]([N:26]([CH3:27])[CH3:28])=[O:25])[CH:22]=[CH:23][C:15]=3[CH2:14]2)[CH:3]=1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 71255454HCID 71255454, compound

Product 1

HCID 71255083HCID 71255083, compound

Conditions

Temperature
180 °C

Procedure

The mixture of 2-(4,6-dichloroquinolin-2-yl)-N,N-dimethyl-2,3,4,5-tetrahydro-1H-2-benzazepine-7-carboxamide (133 mg, 0.32 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 11 mg of product as a white solid. MS obsd. (ESI+) [(M+H)+] 438. 1H NMR (400 MHz, CD3OD) δ ppm 7.89 (s, 1 H), 7.60 (d, J=8.0 Hz, 1 H), 7.49 (d, J=8.8 Hz, 1 H), 7.38 (m, 1 H), 7.22 (m, 2 H), 6.01 (s, 1 H), 4.80 (s, 2 H), 4.16 (m, 2 H), 3.44 (t, J=6.4 Hz, 2 H), 3.11-2.97 (m, 10 H), 1.93 (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-d2652dbbff054899b128bcb31310ec5a
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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