Diisopropylethylamine → HCID 53259790, compound

HRID 41578Notes

Reaction equation

HRID 41578 reaction equation
[N:1]1[N:2]([C:6]2[CH:24]=[CH:23][CH:22]=[CH:21][C:7]=2[CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][C:11]3([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[C:10]2=[O:20])[N:3]=[CH:4][CH:5]=1.C(N(C(C)C)CC)(C)C.Cl[C:35]1[CH:44]=[N:43][C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[N:36]=1>C(#N)C>[N:1]1[N:2]([C:6]2[CH:24]=[CH:23][CH:22]=[CH:21][C:7]=2[CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][C:11]3([CH2:15][CH2:16][N:17]([C:35]4[CH:44]=[N:43][C:42]5[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=5)[N:36]=4)[CH2:18][CH2:19]3)[C:10]2=[O:20])[N:3]=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2389382-ChloroquinoxalineHCID 672526432-(2-(2H-1,2,3-triazol-2-yl)benzyl)-2,9-diazaspiro[5.5]undecan-1-one

Product 1

HCID 53259790HCID 53259790, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 2-(2-(2H-1,2,3-triazol-2-yl)benzyl)-2,9-diazaspiro[5.5]undecan-1-one (TFA salt) (200 mg, 0.354 mmol, contains 2.0 moleq. TFA) and diisopropylethylamine (0.64 mL, 3.61 mmol) in acetonitrile (1 mL) was added 2-chloroquinoxaline [1448-87-9] (121 mg, 0.72 mmol). The mixture was heated at 120° C. for 40 min under microwave conditions. The reaction mixture was cooled to rt and concentrated under reduced pressure. The crude mixture was purified by flash-column chromatography over silicagel (eluent: gradient 10%-100% ethyl acetate/heptane) to yield the title compound (106 mg, 65%). [1H NMR (400 MHz, DMSO-d6) ♀ ppm 8.81 (s, 1H), 8.11 (s, 2H), 7.80 (d, 1H), 7.59-7.63 (m, 1H), 7.56-7.59 (m, 2H), 7.44-7.55 (m, 2H), 7.33-7.40 (m, 1H), 7.24-7.29 (m, 1H), 4.54 (br. s, 2H), 4.19-4.29 (m, 2H), 3.39-3.49 (m, 2H), 3.13 (t, 2H), 1.99-2.10 (m, 2H), 1.84-1.92 (m, 2H), 1.73-1.83 (m, 2H), 1.54-1.65 (m, 2H); LCMS RtA=1.16, [M+H]+=454.4].

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. concentrationconcentrated under reduced pressure
  3. customThe crude mixture was purified by flash-column chromatography over silicagel (eluent: gradient 10%-100% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-aaab54caa0da4a62803f7274ebda7454
Source dataset
uspto-grants-2013_09
Patent number
US08530648B2

Reaction notes

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