Ethylamine → HCID 11952366, compound

HRID 1669105Notes

Reaction equation

HRID 1669105 reaction equation
Br[C:2]1[N:3]=[N+:4]([O-:17])[C:5]2[CH:14]=[C:13]3[C:9]([CH2:10][CH:11]([CH2:15][OH:16])[CH2:12]3)=[CH:8][C:6]=2[N:7]=1.[CH2:18]([NH2:20])[CH3:19]>COCCOC>[CH2:18]([NH:20][C:2]1[N:3]=[N+:4]([O-:17])[C:5]2[CH:14]=[C:13]3[C:9]([CH2:10][CH:11]([CH2:15][OH:16])[CH2:12]3)=[CH:8][C:6]=2[N:7]=1)[CH3:19]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 11952365HCID 11952365, compound

Product 1

HCID 11952366HCID 11952366, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of bromide 125 (91 mg, 0.31 mmol), 70% ethylamine (0.5 mL) and DME (3 mL) was stirred at 20° C. for 3 h. The mixture was partitioned between EtOAc and aqueous Na2CO3 solution. The organic layer was separated, dried and the solvent evaporated to give compound 126 (74 mg, 92%) as yellow solid: mp (EtOAc) 150° C.; 1H NMR δ 8.07 (s, 1H, H-9), 7.40 (s, 1H, H-5), 5.07 (br s, 1H, NH), 3.64-3.72 (m, 2H, CH2O), 3.50-3.58 (m, 2H, CH2N), 3.11-3.21 (m, 2H, CH2), 2.71-2.93 (m, 3H, CH2, CH), 1.29 (t, J=7.2 Hz, 3H, CH3), OH not observed; HRMS calcd for C13H16N4O2 (M+) m/z 260.1271, found 260.1273.

Workup

  1. customThe mixture was partitioned between EtOAc and aqueous Na2CO3 solution
  2. customThe organic layer was separated
  3. customdried
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-ae5336aaf8364e6eba599b2f3552d47c
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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