Sodium Bicarbonate → HCID 178501156, compound

HRID 643445Notes

Reaction equation

HRID 643445 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([CH2:9][NH2:10])=[N:4][N:3]=1.C([O-])(O)=O.[Na+].O=C1CCC(=O)N1[O:23][C:24]([C@H:26]1[CH2:31][CH2:30][C@H:29]([C:32]([O:34][CH3:35])=[O:33])[CH2:28][CH2:27]1)=O.C1COCC1.CC#N>O>[NH2:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([CH2:9][NH:10][C:24]([C@H:26]2[CH2:27][CH2:28][C@H:29]([C:32]([O:34][CH3:35])=[O:33])[CH2:30][CH2:31]2)=[O:23])=[N:4][N:3]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 22177404Acetonitrile tetrahydrofuranHCID 135742493HCID 135742493, compoundHCID 178501165HCID 178501165, compound

Product 1

HCID 178501156HCID 178501156, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 3-amino-6-(aminomethyl)-1,2,4-triazin-5(4H)-one [J. Heterocyclic Chem., (1984), 21 (3), 697] (2.00 g, 0.0113 mol) in H2O (60.0 mL, 3.33 mol) was cooled to 0° C. and drop wise charged with 1.00 M of NaHCO3 in H2O (22.5 mL) and allowed to warm to rt. This mixture was charged with methyl trans-4-{[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}cyclohexanecarboxylate (3.8 g, 0.012 mol) in 1:1 THF/MeCN (40 mL). After 30 min a precipitate began to form in the reaction. This was allowed to stir at rt for an additional 16 h and was filtered through a fritted funnel and washed with H2O (2×), diethyl ether (2×), and dried in vacuo resulting in the title compound 2.92 g, (84% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.24-1.55 (m, 4H), 1.83 (s, 2H), 1.98 (d, J=10.61 Hz, 2H), 2.27 (s, 2H), 3.64 (s, 3H), 4.10 (d, J=5.81 Hz, 21H), 6.81 (br. s., 2H), 7.91 (t, J=5.56 Hz, 1H) and 11.98 (br. s., 1H); MS (ES+): m/z 310.05 [MH+].

Workup

  1. customto form in the reaction
  2. filtrationwas filtered through a fritted funnel
  3. washwashed with H2O (2×), diethyl ether (2×)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-79a6d81fe95940d5b387bf396f9eaa0e
Source dataset
uspto-grants-2010_04
Patent number
US07700594B2

Reaction notes

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