Isoamylamine → HCID 11698196, compound

HRID 2074130Notes

Reaction equation

HRID 2074130 reaction equation
C(O[C:4]([C:6]1[S:7][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:28])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:27])([F:26])[F:25])[CH2:13][CH2:12]2)=[N:9][N:10]=1)=[O:5])C.[CH2:29]([NH2:34])[CH2:30][CH:31]([CH3:33])[CH3:32].[C-]#N.[Na+]>>[CH3:32][CH:31]([CH3:33])[CH2:30][CH2:29][NH:34][C:4]([C:6]1[S:7][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:28])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:25])([F:27])[F:26])[CH2:13][CH2:12]2)=[N:9][N:10]=1)=[O:5]

Participants

4

Reactant 3

HCID 7894IsoamylamineHCID 8929Sodium CyanideHCID 115823885-[4-(2-Trifluoromethylbenzoyl)piperazin-1-YL]-[1,3,4]thiadiazole-2-carboxylic acid ethyl ester

Product 1

HCID 11698196HCID 11698196, compound

Procedure

5-[4-(2-Trifluoromethylbenzoyl)piperazin-1-yl][1,3,4]thiadiazole-2-carboxylic acid ethyl ester (0.100 g, 0.24 mmol) was added to the mixture of isoamylamine (2 mL) and sodium cyanide (0.023 g, 0.48 mmol). The reaction mixture was stirred for 16 hours at room temperature and then evaporated to dryness. The residue was redissolved in 50 mL of ethyl acetate and the solution was washed sequentially with water (2×15 mL), brine (2×15 mL), then dried over anhydrous Na2SO4, and concentrated. The title compound was obtained as a white powder in quantitative yield (0.110 g). 1H NMR (500 MHz, CDCl3) δ 7.73 (d, J=7.8 Hz, 1H), 7.62 (dd, J=7.5, 7.5 Hz, 1H), 7.55 (dd, J=7.5, 7.5 Hz, 1H), 7.34 (d, J=7.5 Hz, 1H), 7.01 (t, J=7.8 Hz, 1H), 4.03-4.08 (m, 1H), 3.85-3.91 (m, 1H), 3.62-3.74 (m, 2H), 3.51-3.55 (m, 2H), 3.40-3.46 (m, 2H), 3.32-3.35 (m, 2H), 1.61-1.69 (m, 2H), 1.45-1.51 (m, 1H), 0.92 (d, J=6.6 Hz, 6H). MS (ES+) m/z 456.4 (M+1).

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was redissolved in 50 mL of ethyl acetate
  3. washthe solution was washed sequentially with water (2×15 mL), brine (2×15 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f8da5bf5af2843fe970804b2752623c2
Source dataset
uspto-grants-2011_04
Patent number
US07919496B2

Reaction notes

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