Diisopropylamine → HCID 178491390, compound

HRID 2054472Notes

Reaction equation

HRID 2054472 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[N:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1.[CH:20]1([C:25]2[NH:26][C:27]3[C:33]([C:34](OC)=[O:35])=[CH:32][CH:31]=[C:30]([O:38][CH3:39])[C:28]=3[N:29]=2)[CH2:24][CH2:23][CH2:22][CH2:21]1>O1CCCC1>[CH:20]1([C:25]2[NH:26][C:27]3[C:33]([C:34](=[O:35])[CH2:19][C:16]4[CH:17]=[CH:18][N:13]=[CH:14][CH:15]=4)=[CH:32][CH:31]=[C:30]([O:38][CH3:39])[C:28]=3[N:29]=2)[CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 79634-MethylpyridineHCID 178418339ButyllithiumHCID 178498256HCID 178498256, compound

Product 1

HCID 178491390HCID 178491390, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

A solution of diisopropylamine (0.47 ml) in tetrahydrofuran (6 ml), cooled to −10° C., was treated dropwise, with a solution of butyl lithium in hexanes (1.2 ml, 2.5 M). The resulting solution was stirred for 10 minutes, then cooled to −78° C. and then treated dropwise with a solution of 4-picoline (0.29 ml) in tetrahydrofuran (1 ml). This solution was stirred for 30 minutes then treated with a solution of methyl 2-cyclopentyl-7-methoxy-3H-benzimidazole-4-carboxylate [0.274 g, Reference Example 3(t)] in tetrahydrofuran (2 ml). The cold bath was removed and the reaction mixture stirred for 15 minutes at ambient temperature. The mixture was quenched with water, then diluted with ethyl acetate. The organic phase was separated then washed with brine, then dried over magnesium sulphate and then evaporated. The residue was subjected to flash chromatography on silica, eluting with a mixture of methanol and dichloromethane (8:92, v/v), to give the title compound (0.126 g) as a white solid. [Elemental analysis:—C, 71.7; H, 6.40; N, 12.5%. Calculated:—C, 71.6; H, 6.31; N, 12.5%]. NMR (CDCl3): δ 1.63-2.05(m, 6H), 2.2(m, 2H), 3.33(m, 1H), 4.11(s, 3H), 4.35(s, 2H), 6.72(d, J=8 Hz, 1H), 7.23(m, 2H), 7.82(d, J=8 Hz, 1H), 8.6(m, 2H).

Workup

  1. stirringThis solution was stirred for 30 minutes
  2. customThe cold bath was removed
  3. stirringthe reaction mixture stirred for 15 minutes at ambient temperature
  4. customThe mixture was quenched with water
  5. additiondiluted with ethyl acetate
  6. customThe organic phase was separated
  7. washthen washed with brine
  8. dry with materialdried over magnesium sulphate
  9. customevaporated
  10. washeluting with a mixture of methanol and dichloromethane (8:92

Sources & evidence

ORD record
ord-71e66bcc6b9a469d9282222aad591214
Source dataset
uspto-grants-2008_02
Patent number
US07329675B2

Reaction notes

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