Pyridine → HCID 178527116, compound

HRID 392978Notes

Reaction equation

HRID 392978 reaction equation
[S:1](Cl)(Cl)=[O:2].[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:23]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[C:22]3[CH:30]=[CH:31][C:32]([C:34](=[N:36][OH:37])[NH2:35])=[CH:33][C:21]=3[N:20]=2)=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.N1C=CC=CC=1>O1CCCC1>[CH2:5]([O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[N:23]([CH:24]3[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]3)[C:22]3[CH:30]=[CH:31][C:32]([C:34]4[NH:35][S:1](=[O:2])[O:37][N:36]=4)=[CH:33][C:21]=3[N:20]=2)=[CH:17][CH:18]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 739963422-[4-(Benzyloxy)phenyl]-1-cyclohexyl-N'-hydroxy-1H-benzimidazole-5-carboximidamide

Product 1

HCID 178527116HCID 178527116, compoundYield 39.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Thionyl chloride (0.010 mL, 0.14 mmol) was added dropwise to a suspension of 2-[4-(Benzyloxy)phenyl]-1-cyclohexyl-N′-hydroxy-1H-benzimidazole-5-carboximidamide (0.025 g, 0.057 mmol, see above for preparation) and pyridine (0.020 mL, 0.25 mmol) in tetrahydrofuran (2 mL) at 0° C. The resulting solution was stirred for 3 h, and then concentrated on a rotary evaporator. As starting material remained, the residue was resubjected to the reaction conditions (0.020 mL thionyl chloride and 0.040 mL pyridine). The residue was purified by reverse phase HPLC (C18 column, water/acetonitrile gradient containing 0.05% trifluoroacetic acid) to afford the product as a yellow solid (0.011 g, 32%). 1H NMR (CD3OD) δ 8.32 (d, 1H, J=8.8 Hz), 8.25 (s, 1H), 8.04 (d, 1H, J=8.8 Hz), 7.77 (d, 2H, J=9.1 Hz), 7.49 (d, 2H, J=6.6 Hz) 7.43-7.35 (m, 5H), 5.27 (s, 2H), 4.55 (m, 1H), 2.45 (m, 2H), 2.15 (m, 2H), 2.00 (m, 2H), 1.80 (m, 1H), 1.44 (m, 3H); ESI-MS m/e 487.3 (M+1); HPLC purity (ELSD)>95%.

Workup

  1. concentrationconcentrated on a rotary evaporator
  2. customthe residue was resubjected to the reaction conditions (0.020 mL thionyl chloride and 0.040 mL pyridine)
  3. customThe residue was purified by reverse phase HPLC (C18 column, water/acetonitrile gradient containing 0.05% trifluoroacetic acid)

Sources & evidence

ORD record
ord-d5882848e0a34247be857cb7e0002250
Source dataset
uspto-grants-2004_10
Patent number
US06803374B2

Reaction notes

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