Water → HCID 46848521, compound

HRID 929420Notes

Reaction equation

HRID 929420 reaction equation
Br[CH2:2][C:3](=O)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:16]([NH:23][C:24]([NH2:26])=[NH:25])([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].O>CN(C=O)C>[NH2:26][C:24]1[N:23]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:2]=[C:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 86708851HCID 86708851, compoundHCID 178454308HCID 178454308, compound

Product 1

HCID 46848521HCID 46848521, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-bromo-7-phenylheptan-2-one (1.00 g, 3.71 mmol) was placed in a 50 mL round bottomed flask with a stir bar and dissolved in 10 mL of DMF. Boc guanidine (1.77 g, 11.13 mmol) was then added to the reaction mixture and it was allowed to stir for 48 hours. Water was then added to the reaction mixture and it was placed in a separatory funnel. The mixture was then extracted twice with ethyl acetate, washed twice with water, washed twice with brine, concentrated de vacuo and then purified via column chromatography (5% methanol/95% dichloromethane) to provide tert-butyl 2-amino-4-(5-phenylpentyl)-1H-imidazole-1-carboxylate as a hygroscopic light yellow solid (0.77 g, 63% yield), 1H NMR (300 MHz, CDCl3) δ 7.31 (m, 2H), δ 7.26 (m, 3H), δ 6.66 (s, 2H), δ 6.51 (s, 1H), δ 2.63 (t, J=7.5 Hz, 2H), δ 2.39 (t, J=7.5 Hz, 2H), δ 1.67 (m, 4H), δ 1.53 (s, 9H), δ 1.40 (m, 2H) ppm; 13C NMR (75 MHz, CDCl3) δ 151.1, 149.8, 143.0, 130.3, 128.7, 128.5, 125.8, 106.2, 84.5, 36.1, 31.6, 29.2, 28.5, 28.4, 28.2 ppm; IR νmax (cm−1) 3433, 2098, 1639, 1454, 1204; HRMS (ESI) calcd for C19H27N3O2 (M+) 329.2103, found 329.2109. Then, tert-butyl 2-amino-4-(5-phenylpentyl)-1H-imidazole-1-carboxylate was dissolved in a 1:4 mixture of trifluoroacetic acid/dichloromethane and allowed to stir for five hours and then concentrated de vacuo. The sample was then dissolved with a dilute HCl/methanol (5 drops HCl/50 mL of methanol) and then concentrated de vacuo to provide 4-(5phenylpentyl)-1H)-imidazol-2-amine hydrochloride as a hygroscopic light yellow solid (0.62 g, 63% overall yield). 1H NMR (300 MHz, CD3OD) δ 7.20 (t, J=7.2 Hz, 2H), δ 7.12 (d, J=7.2 Hz, 3H), δ 6.37 (s, 1H), δ 2.56 (t, J=7.5 Hz, 2H), δ 2.41 (t, J=7.5 Hz, 2H), δ 1.57 (m, 4H), δ 1.34 (m, 2H) ppm; 13C NMR (75 MHz, CDCl3) δ 147.3, 142.5, 128.3, 128.1, 127.7, 125.6, 108.2, 35.5, 31.1, 28.3, 27.0, 24.2 ppm; IR νmax (cm−1) 3385, 2933, 2857, 1679, 1536, 1495, 1453, 1335, 1172, 748, 700; HRMS (ESI) calcd for C14H19N3(M+) 229.1578, found 229.1571.

Workup

  1. customwas placed in a separatory funnel
  2. extractionThe mixture was then extracted twice with ethyl acetate
  3. washwashed twice with water
  4. washwashed twice with brine
  5. concentrationconcentrated de vacuo
  6. custompurified via column chromatography (5% methanol/95% dichloromethane)

Sources & evidence

ORD record
ord-7c5d01f65f0d4ae0bd471326b463dc42
Source dataset
uspto-grants-2016_03
Patent number
US09295257B2

Reaction notes

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