Triethylamine → HCID 178492074, compound

HRID 720445Notes

Reaction equation

HRID 720445 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=[O:24])[N:15]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]#[N:23])[CH2:16][CH2:17][C:12]=3[C:11]([C:25]([F:28])([F:27])[F:26])=[N:10]2)=[CH:5][CH:4]=1.Cl.[NH2:30][OH:31].C(N(CC)CC)C>C(O)C>[OH:31][NH:30][C:22](=[NH:23])[CH2:21][CH2:20][CH2:19][CH2:18][N:15]1[CH2:16][CH2:17][C:12]2[C:11]([C:25]([F:28])([F:26])[F:27])=[N:10][N:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C:13]=2[C:14]1=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 10023400HCID 10023400, compound

Product 1

HCID 178492074HCID 178492074, compoundYield 414.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-[1-(4-Methoxy-phenyl)-7-oxo-3-trifluoromethyl-1,4,5,7-tetrahydro-pyrazolo[3,4-c]pyridin-6-yl]-pentanenitrile (0.100 g, 0.255 mmol), hydroxylamine hydrochloride (0.027 g, 0.382 mmol), and triethylamine (0.071 mL, 0.510 mmol) were dissolved in ethanol (10 mL). The reaction was refluxed overnight, concentrated, and purified by reverse HPLC and freeze-drying to afford the title compound (0.45 g, 42%): 1H NMR (CHCl3) δ 7.61 (bs, 0.5 H), 7.38 (d, j=8.5 Hz, 2H), 6.94 (d, j=8.8 Hz, 2H), 6.72 (bs, 0.5H), 3.82 (s, 3H), 3.68 (t, j=6.4 Hz, 2H), 3.48 (s, 2H), 3.01 (t, j=6.4 Hz, 2H), 3.35 (s, 3H), 1.56 (bs, 4H) ppm; Mass Spec 426.3(M+H)+.

Workup

  1. temperatureThe reaction was refluxed overnight
  2. concentrationconcentrated
  3. custompurified by reverse HPLC
  4. customfreeze-drying

Sources & evidence

ORD record
ord-c972b6751332489c9b37375afb700de1
Source dataset
uspto-grants-2006_11
Patent number
US07135469B2

Reaction notes

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