Morpholine → HCID 57708176, compound

HRID 643702Notes

Reaction equation

HRID 643702 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([C:17]([CH3:22])([CH3:21])[C:18]([OH:20])=O)(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:3][CH2:2]1.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.CCN(C(C)C)C(C)C.C(P(=O)(OCC)OCC)#N>CN(C=O)C>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([C:17]([CH3:21])([CH3:22])[C:18]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[O:20])(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:23][C:24]([CH3:25])([CH3:27])[CH3:26])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 76257Diethyl cyanophosphonateHCID 81531DiisopropylethylamineHCID 59253266HCID 59253266, compound

Product 1

HCID 57708176HCID 57708176, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-{[1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazol-5-yl]sulfonyl}-2-methylpropanoic acid (Example 1, Step H, 180 mg, 0.46 mmol), morpholine (Wako Pure Chemical Industries, Ltd., 48 mg, 0.55 mmol), N,N′-diisopropylethylamine (71 mg, 0.55 mmol) in N,N′-dimethylformamide (3 mL) was added diethyl cyanophosphonate (Aldrich, 90 mg, 0.55 mmol) at room temperature. The mixture was stirred at room temperature for 20 h and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:4 as eluent) to afford the title compound (102 mg, 48%) as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:4 as eluent)

Sources & evidence

ORD record
ord-cb5c1ee343f4433e8046bf77c5e4568f
Source dataset
uspto-grants-2010_04
Patent number
US07700618B2

Reaction notes

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