Isobutyl chloroformate → HCID 10200601, compound

HRID 898711Notes

Reaction equation

HRID 898711 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.Cl[C:24]([O:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[O:25]>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:24]([O:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[O:25])[C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)[CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 62365Isobutyl chloroformateHCID 50257392-((4-(2-Pyridinyl)-1-piperazinyl)methyl)-1H-benzimidazole

Product 1

HCID 10200601HCID 10200601, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Example 1A (0.77 g, 2.6 mmol) in dichloromethane (7 mL) was added isobutyl chloroformate (0.375 mL, 2.9 mmol). The mixture was stirred at room temperature for 16 hours, concentrated under reduced pressure and the residue was purified by flash column on SiO2 eluting with 1.3% methanol/dichloromethane to give 0.5 g (49%) of the title compound as an oil. 1H NMR (CDCl3, 300 MHz) δ 1.10 (d, J=6 Hz, 6H), 2.22 (m, 1H), 2.86 (bm, 4H), 3.67 (bm, 4H), 4.18 (bs, 2H), 4.33 (d, J=7 Hz, 2H), 6.66 (m, 2H), 7.35 (m, 2H), 7.53 (m, 1H), 7.76 (m, 1H), 7.93 (m, 1H), 8.19 (m, 1H). MS (DCI/NH3) m/z 394 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe residue was purified by flash column on SiO2 eluting with 1.3% methanol/dichloromethane

Sources & evidence

ORD record
ord-be2d1c6d50144fabb562570858d37301
Source dataset
uspto-grants-2008_04
Patent number
US07351828B2

Reaction notes

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