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

HRID 570600Notes

Reaction equation

HRID 570600 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]=[C:14]=S)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C1(C([O-])=O)C=C(C)C=C(C)C=1.[NH2:27][N+:28]1[CH:33]=[CH:32][N:31]=[CH:30][C:29]=1[NH2:34].C(N(C(C)C)CC)(C)C.CCN=C=NCCCN(C)C.[ClH:55]>ClCCl>[Cl:55][C:30]1[C:29]2[N:28]([N:27]=[C:14]([NH:13][C:10]3[CH:11]=[CH:12][C:7]([N:4]4[CH2:5][CH2:6][O:1][CH2:2][CH2:3]4)=[CH:8][CH:9]=3)[N:34]=2)[CH:33]=[CH:32][N:31]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2248624-(4-Isothiocyanatophenyl)morpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 1317328011,2-Diamino-pyrazinium mesitylenate

Product 1

HCID 866943398-Chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-yl-(4-morpholin-4-yl-phenyl)-amineYield 84.17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-morpholinophenylisothiocyanate (2 g, 8.99 mmol) in dry dichloromethane (200 ml), 1,2-diamino-pyrazinium mesitylenate (3.86 g, 11.24 mmol), diisopropylethylamine (5.81 g, 44.99 mmol) and EDCl (3.44 g, 17.98 mmol) are added and stirred for 6 hours. The reaction mixture is concentrated and the residue is taken in water (100 ml), triturated and filtered, washed with water (50 ml×2) and dried, the crude solid is purified by silica column using (60-120) mesh to get the titled product as light brown solid (2.5 g, 84.17%); TLC: chloroform/methanol (9.5/0.5) Rf-0.3; HPLC purity (method A) 98%; Rt (min): 2.21; LCMS: mass found (M+, 331.0), Rt (min): 2.08;

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customtriturated
  3. filtrationfiltered
  4. washwashed with water (50 ml×2)
  5. customdried
  6. customthe crude solid is purified by silica column

Sources & evidence

ORD record
ord-203a19c74d5e4e65b7b74bdfa40d9030
Source dataset
uspto-grants-2015_05
Patent number
US09023851B2

Reaction notes

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