Triethylamine → HCID 72195115, compound

HRID 2406359Notes

Reaction equation

HRID 2406359 reaction equation
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].O[NH:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]2([CH2:19][C:18]3([O:37][C:22]4=[CH:23][N:24]=[C:25]([C:27]5[CH2:28][CH2:29][N:30]([S:33]([CH3:36])(=[O:35])=[O:34])[CH2:31][CH:32]=5)[CH:26]=[C:21]4[CH2:20]3)[CH2:17]2)[CH2:13][CH2:12]1)=[NH:10].C(N(CC)CC)C>O1CCCC1.CO>[CH:2]([C:1]1[O:5][N:10]=[C:9]([N:11]2[CH2:16][CH2:15][C:14]3([CH2:17][C:18]4([O:37][C:22]5=[CH:23][N:24]=[C:25]([C:27]6[CH2:32][CH2:31][N:30]([S:33]([CH3:36])(=[O:34])=[O:35])[CH2:29][CH:28]=6)[CH:26]=[C:21]5[CH2:20]4)[CH2:19]3)[CH2:13][CH2:12]2)[N:8]=1)([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 178504930HCID 178504930, compound

Product 1

HCID 72195115HCID 72195115, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

Isobutyryl chloride (10 μL) is added to a solution of 1″-(hydroxycarbamimidoyl)-5-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1′-cyclobutane-3′,4″-piperidine] (40 mg) and triethylamine (41 μL) in tetrahydrofuran (3 mL) at room temperature. The solution is stirred at room temperature for 1 h and at 45° C. overnight. The solution is diluted with methanol and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 3:7→1:9) to give the title compound. LC (method 4): tR=1.13 min; Mass spectrum (ESI+): m/z=500 [M+H]+.

Workup

  1. concentrationconcentrated
  2. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 3:7→1:9)

Sources & evidence

ORD record
ord-ac5205aa4d1349909131edaf2f9fdf04
Source dataset
uspto-grants-2014_08
Patent number
US08809361B2

Reaction notes

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