Diisopropylethylamine → HCID 178418888, compound

HRID 7087Notes

Reaction equation

HRID 7087 reaction equation
[C:1]([C:9]1[CH:19]=[CH:18][C:12]2[N:13]=[C:14]([CH2:16]Cl)[NH:15][C:11]=2[CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC([N:27]([CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][N:49]=1)[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][NH:36][CH:37]2[C:46]3[N:45]=[CH:44][CH:43]=[CH:42][C:41]=3[CH2:40][CH2:39][CH2:38]2)=[CH:31][CH:30]=1)=O)(C)(C)C.C(N(CC)C(C)C)(C)C>CN(C=O)C>[N:49]1[CH:50]=[CH:51][CH:52]=[CH:53][C:48]=1[CH2:47][NH:27][CH2:28][C:29]1[CH:30]=[CH:31][C:32]([CH2:35][N:36]([CH2:16][C:14]2[NH:13][C:12]3[CH:18]=[CH:19][C:9]([C:1](=[O:8])[C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:10][C:11]=3[N:15]=2)[CH:37]2[C:46]3[N:45]=[CH:44][CH:43]=[CH:42][C:41]=3[CH2:40][CH2:39][CH2:38]2)=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1951252[2-(chloromethyl)-1H-benzimidazol-5-yl](phenyl)methanoneHCID 22018600N-(t-butoxycarbonyl)-N-(2-pyridinylmethyl)-N'-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

Product 1

HCID 178418888HCID 178418888, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-benzoyl-2-chloromethylbenzimidazole (284 mg, 1.05 mmol), N-(tert-butoxycarbonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (476 mg, 1.04 mmol) and N,N-diisopropylethylamine (0.36 mL, 2.08 mmol) were stirred at 80□ C in DMF (4 mL) for 16 hours. The reaction was then cooled, concentrated under reduced pressure and diluted with CH2Cl2 (35 mL) and saturated aqueous NaHCO3 (40 mL). The phases were separated and the aqueous phase was washed with CH2Cl2 (2×25 mL). The combined organic extracts were washed with saturated aqueous NaHCO3 (1×40 mL), dried (NaSO4), filtered and concentrated under reduced pressure. Purification of the resultant oil by flash chromatography on silica gel (96:4 CH2Cl2/MeOH) provided the desired alkylated product (468 mg, 65%) as an orange oil.

Workup

  1. temperatureThe reaction was then cooled
  2. concentrationconcentrated under reduced pressure
  3. additiondiluted with CH2Cl2 (35 mL) and saturated aqueous NaHCO3 (40 mL)
  4. customThe phases were separated
  5. washthe aqueous phase was washed with CH2Cl2 (2×25 mL)
  6. washThe combined organic extracts were washed with saturated aqueous NaHCO3 (1×40 mL)
  7. dry with materialdried (NaSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customPurification of the resultant oil by flash chromatography on silica gel (96:4 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-c3e65d3523c4435f91103dac99cfb3aa
Source dataset
uspto-grants-2006_08
Patent number
US07084155B2

Reaction notes

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