Diisopropylethylamine → 8-Bromo-(1,2,4)triazolo(1,5-a)pyridin-2-amine

HRID 570557

Reaction equation

HRID 570557 reaction equation
Cl.NO.C([N:7](CC)C(C)C)(C)C.[Br:13][C:14]1[C:15]([NH:20][C:21]([NH:23]C(OCC)=O)=S)=[N:16][CH:17]=[CH:18][CH:19]=1>CO.C(O)C>[Br:13][C:14]1[C:15]2[N:16]([N:7]=[C:21]([NH2:23])[N:20]=2)[CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 59199107Ethyl aminon-(3-bromopyridin-2-YL)methanethiocarbamate

Product 1

HCID 468640698-Bromo-(1,2,4)triazolo(1,5-a)pyridin-2-amine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a stirred suspension of hydroxylamine hydrochloride (about 17 g) and N,N-diisopropylethylamine (about 26 mL) in a mixture of methanol (about 70 mL) and ethanol (about 70 mL) is added N-(3-bromo-2-pyridinyl)-N′-carboethoxy-thiourea. The mixture is stirred for about 2 hours at room temperature then heated to about 60° C. for about 18 hours. The suspension is cooled to room temperature, filtered and rinsed with methanol, water then methanol. 8-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine is isolated as an off-white solid (about 8 g). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 8.58 (d, J=6.4 Hz, 1H), 7.73 (d, J=7.6 Hz, 1H), 6.80 (t, J=7.0 Hz, 1H), 6.25 (s, 2H). MS=213, 215 (MH)+.

Workup

  1. temperaturethen heated to about 60° C. for about 18 hours
  2. temperatureThe suspension is cooled to room temperature
  3. filtrationfiltered
  4. washrinsed with methanol, water

Sources & evidence

ORD record
ord-94896074d91948fcb85aad83f9e7cf32
Source dataset
uspto-grants-2015_05
Patent number
US09023853B2

Linked notes

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