HCID 67061930, compound → HCID 178478698, compound

HRID 242365Notes

Reaction equation

HRID 242365 reaction equation
[ClH:1].Cl.NCCCC1N=C(N)NC=1.C(OC([N:20]1[CH:24]=[C:23]([CH2:25][CH2:26][CH2:27][C:28](=O)[NH:29]C2CCCC2)[N:22]=[C:21]1[NH2:36])=O)(C)(C)C>>[ClH:1].[ClH:1].[NH2:29][CH2:28][CH2:27][CH2:26][CH2:25][C:23]1[N:22]=[C:21]([NH2:36])[NH:20][CH:24]=1

Participants

3

Reactant 2

HCID 67061930HCID 67061930, compoundHCID 178478696HCID 178478696, compound

Product 1

HCID 178478698HCID 178478698, compoundYield 18%

Procedure

Using the same general procedure as used for the synthesis of 4-(3-amino-propyl)-1H-imidazol-2-ylamine dihydrochloride 16, 12.5 g of lysine methyl ester dihydrochloride 28 afforded 2.25 g (18%) of the target compound 29 as a yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 6.09 (s, 1H), 4.96 (s, 2H), 2.56 (t, 2H, J=6.3 Hz), 2.27 (t, 2H, J=6.9 Hz), 1.35-1.51 (m, 4H); 13C NMR (100 MHz, DMSO-d6) δ 149.11, 132.29, 110.59, 40.75, 31.41, 26.62, 26.12; HRMS (ESI) calcd for C7H15N4 (MH+) 155.1291, found 155.1293.

Sources & evidence

ORD record
ord-c97ae2a49db44d92b94f4889d1293671
Source dataset
uspto-grants-2014_02
Patent number
US08653124B2

Reaction notes

Loading…