2-Bromoethyldiethylammonium bromide → HCID 59589796, compound

HRID 1472804Notes

Reaction equation

HRID 1472804 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]3[N:14]=[C:15]([NH:17][C:18]([CH:20]4[CH2:22][CH2:21]4)=[O:19])[N:16]=[C:12]3[CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Br.Br[CH2:25][CH2:26][N:27]([CH2:30][CH3:31])[CH2:28][CH3:29].C(N(C(C)C)CC)(C)C>>[CH2:26]([N:27]([CH2:30][CH3:31])[CH2:28][CH2:29][NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]3[N:14]=[C:15]([NH:17][C:18]([CH:20]4[CH2:21][CH2:22]4)=[O:19])[N:16]=[C:12]3[CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1)[CH3:25]

Participants

4

Reactant 3

HCID 706072-Bromoethyldiethylammonium bromideHCID 81531DiisopropylethylamineHCID 59179470HCID 59179470, compound

Product 1

HCID 59589796HCID 59589796, compound

Conditions

Temperature
150 °C

Procedure

Cyclopropanecarboxylic acid [5-(4-amino-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-amide (0.05 g, 0.17 mmol), 2-bromo-N,N-diethylethylamine hydrobromide (0.133 g, 0.511 mmol) and diisopropylethylamine (0.089 mL, 0.511 mmol) were added to a microwave tube and the mixture was heated for 10 min at 150° C. The mixture was filtered and purified by preparatory LCMS. LCMS Method: 2: RT: 2.07 min; MI: 393 [M+1]. NMR (DMSO, 300 MHz): 0.81 (d, 4H), 1.10 (t, 6H), 2.04 (brs, 1H), 2.89 (m, 6H), 3.33 (t, 2H), 6.75 (d, 2H), 7.20 (dd, 1H), 7.53 (m, 1H), 7.64 (m, 1H), 7.92 (d, 2H), 8.18 (s, 1H), 11.00 (s, 1H)

Workup

  1. filtrationThe mixture was filtered
  2. custompurified by preparatory LCMS

Sources & evidence

ORD record
ord-14ebd0ab16224267a5059a26ef5800cd
Source dataset
uspto-grants-2015_04
Patent number
US09012633B2

Reaction notes

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