Diisopropylethylamine → HCID 70896232, compound

HRID 2369905Notes

Reaction equation

HRID 2369905 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@H:3]([NH:9][CH2:10][CH2:11][N:12]1[C:16]3[C:17]([C:21]([O-])=[O:22])=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]=[CH:13]1)[CH2:2]2.[Li+].C(N(CC)C(C)C)(C)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>CN(C)C=O>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@H:3]([N:9]1[C:21](=[O:22])[C:17]3[CH:18]=[CH:19][CH:20]=[C:15]4[N:14]=[CH:13][N:12]([C:16]=34)[CH2:11][CH2:10]1)[CH2:2]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 66899496HCID 66899496, compound

Product 1

HCID 70896232HCID 70896232, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of lithium (S)-1-(2-(quinuclidin-3-ylamino)ethyl)-1H-benzo[d]imidazole-7-carboxylate (0.2 g, 0.7 mmol) from Step G above, N,N-diisopropylethylamine (0.7 mL, 4.1 mmol), and 1-propanephosphonic acid cyclic anhydride (T3P) (2.1 mL, 3.4 mmol) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 7 h. The crude reaction was concentrated under reduced pressure and then purified by SCX column and preparative thin layer chromatography (90:9:1 methylene chloride/methanol/ammonium hydroxide) to afford 6-((S)-quinuclidin-3-yl)-5,6-dihydroimidazo[4,5,1-jk][1,4]benzodiazepin-7(4H)-one: 1H NMR (500 MHz, DMSO-d6) δ 8.32 (s, 1H), 7.91 (d, J=8.0 Hz, 1H), 7.86 (dd, J=8.0, 1.0 Hz, 1H), 7.32 (t, J=8.0 Hz, 1H), 4.85-4.50 (m, 2H), 4.48-4.39 (m, 2H), 3.91-3.33 (m, 1H), 3.31-3.11 (m, 1H), 3.08-3.02 (m, 1H), 2.99-2.89 (m, 1H), 2.81-2.71 (m, 3H), 1.97-1.95 (m, 1H), 1.71-1.56 (m, 3H), 1.49-1.39 (m, 1H).

Workup

  1. customThe crude reaction
  2. concentrationwas concentrated under reduced pressure
  3. custompurified by SCX column and preparative thin layer chromatography (90:9:1 methylene chloride/methanol/ammonium hydroxide)

Sources & evidence

ORD record
ord-13a761335cab4e50a001a0ef918f02b0
Source dataset
uspto-grants-2014_04
Patent number
US08710046B2

Reaction notes

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