Cyclohexanecarboxylic acid → HCID 136102522, compound

HRID 1993156Notes

Reaction equation

HRID 1993156 reaction equation
[NH2:1][CH2:2][C:3]1[C:4](=[O:9])[NH:5][CH:6]=[N:7][N:8]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[CH:32]1([C:38](O)=O)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1.C(N(CC)C(C)C)(C)C.P(Cl)(Cl)(Cl)=O>CN(C=O)C.C(#N)C>[CH:32]1([C:38]2[N:8]3[C:3]([C:4](=[O:9])[NH:5][CH:6]=[N:7]3)=[CH:2][N:1]=2)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

8

Reactant 5

HCID 7413Cyclohexanecarboxylic acidHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 1357424956-(Aminomethyl)-1,2,4-triazin-5(4H)-one

Product 1

HCID 136102522HCID 136102522, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
55 °C

Procedure

To a suspension of 6-aminomethyl-4H-[1,2,4]triazin-5-one (250 mg, 1.98 mmol) in DMF (7.5 mL) was added 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (760 mg, 2.38 mmol), cyclohexanecarboxylic acid (305 mg, 2.38 mmol) and N,N-diisopropylethylamine (1.5 mL, 8.6 mmol). After 1 h acetonitrile (40 mL) was added to the mixture followed by dropwise addition of phosphoryl chloride (0.28 mL, 3.0 mmol) and the reaction mixture stirred at 55° C. for 1 h. The mixture was then concentrated in vacuo chromatographed over silica gel eluting with 3% MeOH in DCM, to afford 7-cyclohexylimidazo[5,1-f][1,2,4]triazin-4(3H)-one. 1H NMR (400 MHz—DMSO-d6) δ 1.24-1.91 (m, 10H), 3.08-3.16 (m, 1H), 7.68 (s, 1H) 7.88 (s, 1H) 11.76 (s, 1H); MS (ES+): m/z: 219.24 (100) [MH+]. HPLC: tR=2.44 min (OpenLynx: polar—5 min).

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customchromatographed over silica gel eluting with 3% MeOH in DCM

Sources & evidence

ORD record
ord-faf51558ac404c22867d33d01f876469
Source dataset
uspto-grants-2010_01
Patent number
US07651687B2

Reaction notes

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