Tert-Butyl nitrite → HCID 178501067, compound

HRID 1993250Notes

Reaction equation

HRID 1993250 reaction equation
N[C:2]1[NH:7][C:6](=[O:8])[C:5]2=[C:9]([I:22])[N:10]=[C:11]([C@H:12]3[CH2:17][CH2:16][C@H:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:14][CH2:13]3)[N:4]2[N:3]=1.N(OC(C)(C)C)=O>C1COCC1.CN(C=O)C>[I:22][C:9]1[N:10]=[C:11]([C@H:12]2[CH2:13][CH2:14][C@H:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:16][CH2:17]2)[N:4]2[C:5]=1[C:6](=[O:8])[NH:7][CH:2]=[N:3]2

Participants

5

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 178501068HCID 178501068, compound

Product 1

HCID 178501067HCID 178501067, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl trans-4-(2-amino-5-iodo-4-oxo-3,4-dihydroimidazo[5,1-f][1,2,4]triazin-7-yl)cyclohexanecarboxylate (0.880 g, 0.00211 mol) in anhydrous THF (74 mL) and DMF (13.2 mL) was charged with tert-butyl nitrite (1.2 mL, 0.010 mol) and stirred at rt for 2 h. The reaction was concentrated in vacuo and was purified by chromatography over silica gel [eluting with 5% MeOH in CHCl3] resulting in 570 mg, (67% yield) of the title compound as a pale orange solid. (1H NMR (400 MHz, DMSO-d6) δ ppm 1.40-1.54 (m, 2H), 1.56-1.69 (m, 2H), 1.92-2.06 (m, 4H), 2.36-2.46 (m, 1H), 3.02-3.14 (m, 1H), 3.61 (s, 3H), 7.89 (d, J=3.28 Hz, 1 H) and 11.79 (br. s., 1H); MS (ES+): m/z 402.86 [MH+].

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customwas purified by chromatography over silica gel [eluting with 5% MeOH in CHCl3]

Sources & evidence

ORD record
ord-98bdcd1503e64f64a8d367b64426dece
Source dataset
uspto-grants-2010_01
Patent number
US07651687B2

Reaction notes

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