Ethylenediamine → HCID 71262272, compound

HRID 540350Notes

Reaction equation

HRID 540350 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][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[O:15][CH2:14][CH2:13]2)[CH:3]=1.[CH2:23]([NH2:26])[CH2:24][NH2:25]>>[O:15]1[C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[CH2:18][N:12]([C:4]2[CH:3]=[C:2]([NH:25][CH2:24][CH2:23][NH2:26])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH2:13][CH2:14]1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 71255169HCID 71255169, compound

Product 1

HCID 71262272HCID 71262272, compound

Conditions

Temperature
150 °C

Procedure

The mixture of 4-(4-chloroquinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine (100 mg, 0.32 mmol) and 1.6 mL of ethane-1,2-diamine was heated with stirring in a 5 mL microwave process vial for 3 hours at 150° C. under microwave irradiation. The mixture was concentrate in vacuo to give a residue which was purified by preparative HPLC to give 31 mg of product as a white solid. MS obsd. (ESI+) [(M+H)+] 335. 1H NMR (400 MHz, CD3OD) δ ppm 8.61 (s, 1 H), 7.90 (d, J=7.6 Hz, 1 H), 7.60-7.51 (m, 3 H), 7.23 (brs, 2 H), 7.09-6.98 (m, 2 H), 6.05 (s, 1 H), 4.89 (s, 2 H), 4.27 (s, 2 H), 4.25 (s, 2 H), 3.61 (s, 2 H), 3.15 (s, 2 H).

Workup

  1. temperaturewas heated
  2. concentrationThe mixture was concentrate in vacuo
  3. customto give a residue which
  4. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-4c2bf6f2ba0644dcafef8a489d6bb9d3
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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