Acetic Acid → 5-[4-(Ethylamino)cyclohexen-1-yl]-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine

HRID 1959444Notes

Reaction equation

HRID 1959444 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:19]2[CH2:24][CH2:23][C:22](=O)[CH2:21][CH:20]=2)=[N:6][C:7]=1[C:8]1[O:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:11][N:12]=1.[CH2:26]([NH2:28])[CH3:27].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>ClCCCl.C1COCC1.CS(C)=O>[CH2:26]([NH:28][CH:22]1[CH2:23][CH2:24][C:19]([C:5]2[N:6]=[C:7]([C:8]3[O:9][C:10]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)=[N:11][N:12]=3)[C:2]([NH2:1])=[N:3][CH:4]=2)=[CH:20][CH2:21]1)[CH3:27]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 6341EthylamineHCID 5049666Sodium triacetoxyborohydrideHCID 667447634-[5-Amino-6-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]cyclohex-3-en-1-one

Product 1

HCID 667443825-[4-(Ethylamino)cyclohexen-1-yl]-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amineYield 12.3%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[5-amino-6-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]cyclohex-3-en-1-one (15 mg, 0.045 mmol) in DCE (500 μL) was added a solution of ethaneamine (34 μL, of 2 M, 0.07 mmol) in THF and the reaction mixture was stirred for 5 min. Thereafter Na(OAc)3BH (15 mg, 0.07 mmol) was added followed by addition of AcOH (3 mg, 3 μL, 0.05 mmol) and the reaction mixture was stirred for 2 h at room temperature. The crude material was dissolved in DMSO and purified via reverse phase HPLC using 1-99 MeOH/H2O (0.05% HCl modifier) to obtain 5-[4-(ethylamino)cyclohexen-1-yl]-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine (2 mg, 9%) as yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 8.84 (s, 1H), 8.56 (s, 1H), 8.12 (d, J=7.9 Hz, 2H), 7.68 (d, J=7.0 Hz, 3H), 7.60 (s, 1H), 6.58 (s, 1H), 3.05 (dd, J=13.2, 6.6 Hz, 2H), 2.76 (m, 3H), 2.38 (m, 1H), 2.27 (d, J=10.9 Hz, 1H), 1.78 (m, 1H), 1.26 (t, J=7.2 Hz, 3H). LC/MS m/z 363.05 [M+H]+.

Workup

  1. stirringthe reaction mixture was stirred for 2 h at room temperature
  2. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-dad4f6e917f44c0dbce3ce749b83557c
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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