Potassium Iodide → HCID 178420730, compound

HRID 1624272Notes

Reaction equation

HRID 1624272 reaction equation
[N:1]1([C@@H:7]2[CH2:12][CH2:11][C@H:10]([NH:13][CH:14]3[C:23]4[N:22]=[CH:21][CH:20]=[CH:19][C:18]=4[CH2:17][CH2:16][CH2:15]3)[CH2:9][CH2:8]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(OC([N:31]1[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[N:33]=[C:32]1[CH2:40]Cl)=O)(C)(C)C.C(N(CC)C(C)C)(C)C.[I-].[K+]>CC#N>[NH:31]1[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[N:33]=[C:32]1[CH2:40][N:13]([C@H:10]1[CH2:9][CH2:8][C@@H:7]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[CH2:12][CH2:11]1)[CH:14]1[C:23]2[N:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 15829159tert-Butyl 2-(chloromethyl)-1H-benzimidazole-1-carboxylateHCID 178420733HCID 178420733, compound

Product 1

HCID 178420730HCID 178420730, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The above amine (69.0 mg, 0.22 mmol), 2-chloromethyl-benzimidazole-1-carboxylic acid tert-butyl ester (70.0 mg, 0.26 mmol), N,N-diisopropylethylamine (50 μL, 0.28 mmol), and potassium iodide (3.7 mg, 0.02 mmol) in CH3CN (1.5 mL) were stirred at 60° C. overnight. The reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Purification of the crude material by radial chromatography on silica gel (1 mm plate, NH4OH/MeOH/CH2Cl2, 1:1:98 then 1:2:97) afforded the desired compound (56.8 mg, 47%) as a pale yellow solid. 1H NMR (CDCl3) δ 1.30-1.34 (m, 2H), 1.45-1.66 (m, 11H), 1.88-2.01 (m, 4H), 2.05-2.16 (m, 4H), 2.40 (br m, 4H), 2.54 (t, 1H, J=4.4 Hz), 2.59 (t, 1H, J=3.9 Hz), 2.68-2.73 (m, 1H), 3.04-3.11 (m, 1H), 3.61-3.71 (m, 4H), 4.29 (dd, 1H, J=8.7, 5.7 Hz), 4.43 (s, 2H), 6.829 (dd, 1H, J=7.5, 4.8 Hz), 7.07 (d, 1H, J=6.9 Hz), 7.22-7.28 (m, 2H), 7.61-7.70 (m, 1H), 7.73-7.79 (m, 1H), 8.32 (dd, 1H, J=4.8, 1.5 Hz).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customPurification of the crude material by radial chromatography on silica gel (1 mm plate, NH4OH/MeOH/CH2Cl2, 1:1:98

Sources & evidence

ORD record
ord-64d290f04bc545b7891aac5339ca676f
Source dataset
uspto-grants-2014_07
Patent number
US08778967B2

Reaction notes

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