Diethyl acetylenedicarboxylate → HCID 23568416, compound

HRID 1822722Notes

Reaction equation

HRID 1822722 reaction equation
[OH:1][N:2]([CH3:17])[C:3](=[NH:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.[C:18]([C:25]([O:27][CH2:28][CH3:29])=[O:26])#[C:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(O)C>[CH2:28]([O:27][C:25]([C:18]1([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[O:1][N:2]([CH3:17])[C:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[N:16]1)=[O:26])[CH3:29]

Participants

4

Reactant 2

HCID 69803Diethyl acetylenedicarboxylateHCID 22169632HCID 22169632, compound

Product 1

HCID 23568416HCID 23568416, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of N-hydroxy-N-methyl-2-morpholin-4-yl-benzamidine (3.8 g) in ethanol (100 mL, 200 proof) was added diethyl acetylene-dicarboxylate (3.2 mL, 20 mmol) and the resulting mixture stirred at room temperature for 30 min. The mixture was then concentrated and purified on a silica gel column (10%–30% ethyl acetate/hexanes) to afford the title compound (3.64 g, 45% yield). 1HNMR (300 MHz, CDCl3) δ: 7.64 (1H, dd, J=7.69, 1.83 Hz), 7.40 (1H, td, J=8.05, 1.83 Hz), 7.02 (1H, t, J=7.32 Hz), 6.97 (1H, d, J=8.05 Hz) 4.31–4.20 (2H, m), 4.15 (2H, q, J=7.08 Hz), 3.88–3.74 (4H, m), 3.38 (1H, d, J=16.46 Hz), 3.12–2.92 (4H, m), 3.05 (3H, s), 3.03 (1H, d, J=16.47 Hz), 1.29 (3H, t, J=6.95 Hz), 1.25 (3H, t, J=6.96 Hz). HRMS (ESI) calcd for C20H28N3O6 (M+H): 406.1978; found: 406.1975.

Workup

  1. concentrationThe mixture was then concentrated
  2. custompurified on a silica gel column (10%–30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-16573a54dcc94b619c43f8f05a8c153d
Source dataset
uspto-grants-2006_05
Patent number
US07037908B2

Reaction notes

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