HCID 69516187, compound → HCID 178509357, compound

HRID 1297214Notes

Reaction equation

HRID 1297214 reaction equation
[CH:1]1([CH:7]2[CH2:9][C:8]2([C:12]2[N:13]=[N:14][N:15](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:16]=2)[C:10]#[N:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>N.CCO.[Ni]>[CH:1]1([CH:7]2[CH2:9][C:8]2([CH2:10][NH2:11])[C:12]2[NH:16][N:15]=[N:14][N:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 1

HCID 69516187HCID 69516187, compound

Product 1

HCID 178509357HCID 178509357, compoundYield 36%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 702EthanolSolvent

Procedure

To a solution of the 2-cyclohexyl-1-(2-trityl-2H-tetrazol-5-yl)-cyclopropanecarbonitrile (1.10 g, 2.39 mmol) in 50 mL 2.0M NH3 in EtOH was added RaNi (1.4 g), and the mixture was hydrogenated in a Parr shaker at 48 psi for 60 h. The mixture was filtered and concentrated. Flash chromatography of the residue on silica gel (0.25:1.25:3.5 conc. NH4OH (aq):MeOH:CH2Cl2) furnished 0.19 g (36%) of C-[2-cyclohexyl-1-(1H-tetrazol-5-yl)-cyclopropyl]-methylamine as a colorless solid. 1H NMR (CD3OD) δ 3.97 (d, J=13.2 Hz, 1H, —CH2NH2), 2.96 (d, J=13.2 Hz, 1H, —CH2NH2), 1.87 (m, 1H), 1.77 (m, 1H), 1.68 (m, 2H), 1.47 (m, 1H), 1.38 (m, 1H), 1.12-1.31 (m, 6H), 1.07 (m, 1H), 0.91 (dd, J=4.6, 6.6 Hz, 1H, cyclopropyl —CHH). LRMS: m/z 220.2 (M−1). Anal. Calc'd for C11H19N5: C, 59.70; H, 8.65; N, 31.65. Found: C, 58.39; H, 8.54; N, 31.20.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-1901a9abdab3473992dbfa133edb5fa3
Source dataset
uspto-grants-2007_07
Patent number
US07250433B2

Reaction notes

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