Potassium Iodide → HCID 59694184, compound

HRID 899733Notes

Reaction equation

HRID 899733 reaction equation
[N:1]1([CH2:6][CH2:7][NH:8][CH:9]2[C:18]3[N:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:4][N:3]=[CH:2]1.[C:19]([O:23][C:24]([N:26]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[N:28]=[C:27]1[CH2:35]Cl)=[O:25])([CH3:22])([CH3:21])[CH3:20].[I-].[K+].C(N(CC)C(C)C)(C)C.C([O-])(O)=O.[Na+]>C(#N)C>[C:19]([O:23][C:24]([N:26]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[N:28]=[C:27]1[CH2:35][N:8]([CH2:7][CH2:6][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)[CH:9]1[C:18]2[N:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:12][CH2:11][CH2:10]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 15829159tert-Butyl 2-(chloromethyl)-1H-benzimidazole-1-carboxylateHCID 59694102HCID 59694102, compound

Product 1

HCID 59694184HCID 59694184, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (2-imidazol-1-yl-ethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (92 mg, 0.37 mmol), 2-chloromethyl-benzimidazole-1-carboxylic acid tert-butyl ester (101 mg, 0.379 mmol), potassium iodide (3 mg, 0.02 mmol), and N,N-diisopropylethylamine (0.10 mL, 0.57 mmol) in acetonitrile (4 mL) was heated at 60° C. for 15 h. Saturated NaHCO3(aq) (15 mL) was added, and the mixture was extracted with CH2Cl2 (3×15 mL). The combined organic extracts were dried (MgSO4) and concentrated in vacuo. Purification of the crude material by column chromatography on silica gel (250:5:1 CH2Cl2/MeOH/NH4OH) gave a yellow oil (21 mg, 12%). 1H NMR (CDCl3) δ 1.45 (m, 1H), 1.66 (m, 10H), 1.91 (m, 2H), 2.69 (m, 2H), 2.92 (m, 1H), 3.18 (m, 1H), 3.67 (m, 2H), 4.20 (dd, 1H, J=10, 5.6 Hz), 4.67 (d, 1H, J=15 Hz), 4.80 (d, 1H, J=15 Hz), 6.74 (s, 1H), 6.90 (s, 1H), 7.01 (dd, 1H, J=7.7, 4.7 Hz), 7.73 (m, 1H), 7.86 (m, 1H), 8.38 (d, 1H, J=3.3 Hz).

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (3×15 mL)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customPurification of the crude material by column chromatography on silica gel (250:5:1 CH2Cl2/MeOH/NH4OH)

Sources & evidence

ORD record
ord-8b14258fc952445888ac0f72e48e7143
Source dataset
uspto-grants-2008_04
Patent number
US07354934B2

Reaction notes

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