N,N-Dimethylethylenediamine → HCID 90024252, compound

HRID 1048719Notes

Reaction equation

HRID 1048719 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[N:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]3=[N:18][C:17]=2[CH2:25][O:26][C:27]2[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=2[C:29](Cl)=[O:30])=[CH:10][CH:9]=1>ClCCl>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH:5][C:29](=[O:30])[C:28]1[CH:32]=[CH:33][CH:34]=[CH:35][C:27]=1[O:26][CH2:25][C:17]1[N:18]=[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]2[C:16]=1[C:15]#[C:14][C:11]1[CH:12]=[CH:13][C:8]([F:7])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 118195090HCID 118195090, compound

Product 1

HCID 90024252HCID 90024252, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.896 ml (7.76 mmol) of N,N-dimethylethane-1,2-diamine were solubilized in 8 ml of dichloromethane with magnetic stirring, 0.449 g (0.776 mmol) of 2-((3-((4-fluorophenyl)ethynyl)imidazo[1,2-a]pyridin-2-yl)methoxy)benzoyl chloride were added and the mixture was stirred at r.t. for 16 h before being concentrated in vacuo. The crude residue was purified by trituration in 20 ml of diisopropyl ether. The solid was isolated by filtration, washed with 10 ml of water and dried in vacuo. 0.178 g (yield=50%) of N-(2-(dimethylamino)ethyl)-2-((3-((4-fluorophenyl)ethynyl)imidazo[1,2-a]-pyridin-2-yl)methoxy)benzamide were obtained as a pale yellow solid. LC-MS: m/z=457 (MH+); UV purity at 254 nm=98%. 1H NMR (300 MHz, DMSO) δ 8.68 (d, J=6.7 Hz, 1H), 8.47 (d, J=4.8 Hz, 1H), 7.91 (dd, J=7.7, 1.5 Hz, 1H), 7.72 (dd, J=8.6, 5.2 Hz, 3H), 7.57-7.39 (m, 3H), 7.32 (t, J=8.9 Hz, 2H), 7.17 (t, J=6.6 Hz, 1H), 7.09 (t, J=7.3 Hz, 1H), 5.51 (s, 2H), 2.5 (1H hidden under the solvent peak), 2.25 (t, J=6.5 Hz, 2H), 1.92 (s, 6H).

Workup

  1. additionwere added
  2. concentrationbefore being concentrated in vacuo
  3. customThe crude residue was purified by trituration in 20 ml of diisopropyl ether
  4. customThe solid was isolated by filtration
  5. washwashed with 10 ml of water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-a9d7cdfe11b74d5b8727412462c1955c
Source dataset
uspto-grants-2016_07
Patent number
US09381191B2

Reaction notes

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