Triethylamine → HCID 10209100, compound

HRID 1794208Notes

Reaction equation

HRID 1794208 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[NH:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[N:15]=2)[CH2:9][CH2:8]1.[N:23]1([C:28](Cl)=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24]1.C(N(CC)CC)C>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:8][CH2:9][N:10]([CH2:13][C:14]2[N:15]([C:28]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:29])[C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)[CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 709371-Pyrrolidinecarbonyl chlorideHCID 50257392-((4-(2-Pyridinyl)-1-piperazinyl)methyl)-1H-benzimidazole

Product 1

HCID 10209100HCID 10209100, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Example 1A (0.66 g, 2.2 mmol) in dichloromethane (7 mL) was added 1-pyrrolidinecarbonyl chloride (0.28 mL, 2.2 mmol) and triethylamine (0.625 mL, 4.5 mmol). The mixture was heated in a sealed vial for 17 hours, allowed to cool to room temperature, diluted dichloromethane, washed with 5% NaHCO3, dried and concentrated under reduced pressure. The residue was purified by flash column on SiO2 eluting with 20% hexanes/ethyl acetate to give 0.4 g (40%)of the title compound. mp 120–121° C. 1H NMR (CDCl3, 300 MHz) δ 1.79–2.10 (m, 4H), 2.70 (m, 4H), 3.13 (m, 1H), 3.35–3.78 (bm, 8H), 4.32 (m, 1H), 6.65 (m, 2H), 7.30 (m, 3H), 7.49 (m, 1H), 7.76 (m, 1H), 8.28 (m, 1H). MS (DCI/NH3) m/z 391 (M+H)+. Anal. Calcd for C22H26N6.½H2O: C, 66.14; H, 6.81; N, 21.04. Found: C 66.22, H 6.68, N 21.11.

Workup

  1. temperatureThe mixture was heated in a sealed vial for 17 hours
  2. washdiluted dichloromethane, washed with 5% NaHCO3
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column on SiO2 eluting with 20% hexanes/ethyl acetate

Sources & evidence

ORD record
ord-6de25d6cc1204ab8ba04a56cc267b964
Source dataset
uspto-grants-2006_04
Patent number
US07022728B2

Reaction notes

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