Diisopropylethylamine → 8-Chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-yl-(3,5-dimethyl-phenyl)-amine

HRID 570599Notes

Reaction equation

HRID 570599 reaction equation
[C:1]1(C([O-])=O)[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[CH:2]=1.[NH2:12][N+:13]1[CH:18]=[CH:17][N:16]=[C:15]([Cl:19])[C:14]=1[NH2:20].[CH:21]([N:24](C(C)C)CC)(C)C.CCN=C=NCCCN(C)C.Cl>ClCCl.CN(C)C=O>[Cl:19][C:15]1[C:14]2[N:13]([N:12]=[C:21]([NH:24][C:1]3[CH:2]=[C:3]([CH3:8])[CH:4]=[C:5]([CH3:7])[CH:6]=3)[N:20]=2)[CH:18]=[CH:17][N:16]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 1317328001,2-Diamino-3-chloro-pyrazinium mesitylenate

Product 1

HCID 866943458-Chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-yl-(3,5-dimethyl-phenyl)-amineYield 75%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,5-dimethylisothiocyanate (200 mg, 1.2 mmol) in dichloro-methane and N,N-dimethylformamide (1:1) (5.0 mL) were added 1,2-diamino-3-chloro-pyrazinium mesitylenate (0.59 g, 0.0017 mol) and diisopropylethylamine (791 mg, 6.1 mmol). The reaction mixture was stirred for 1 hour. EDCl (93 mg, 5 mmol) was added and the solution stirred for 2 hours at room temperature before being concentrated to dryness. The residue was taken up in water and stirred for 5 minutes and the solid precipitated was filtered, washed with water, dried to get the product as a light brown solid (0.25 g, 75%). TLC: pet ether/ethyl acetate (6/4) Rf-0.4. LCMS (method A): mass found (M+H+, 274.0), Rt (min): 4.47 area % 98.0 (max), 98.47 (254 nm); 1H NMR (400 MHz, DMSO-d6): δ 9.99 (s, 1H), 8.95 (d, J=4.28 Hz, 1H), 7.91 (d, J=4.32 Hz, 1H), 7.28 (s, 2H), 6.58 (s, 1H), 2.24 (s, 6H).

Workup

  1. stirringthe solution stirred for 2 hours at room temperature
  2. concentrationbefore being concentrated to dryness
  3. stirringstirred for 5 minutes
  4. customthe solid precipitated
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-04a51821a35d4bfc924c5a7474484452
Source dataset
uspto-grants-2015_05
Patent number
US09023851B2

Reaction notes

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