Triethylamine → HCID 10099946, compound

HRID 457582Notes

Reaction equation

HRID 457582 reaction equation
C(OP(C#N)(=O)OCC)C.C(N(CC)CC)C.[CH2:18]([S:20]([C:23]1[CH:24]=[CH:25][C:26]([O:50][CH3:51])=[C:27]([NH:29][C:30]2[O:31][C:32]([C:35]3[CH:36]=[C:37]([C:41]4[CH:46]=[CH:45][C:44]([C:47](O)=[O:48])=[CH:43][CH:42]=4)[CH:38]=[CH:39][CH:40]=3)=[CH:33][N:34]=2)[CH:28]=1)(=[O:22])=[O:21])[CH3:19].[CH2:52]1[N:57]([CH2:58][CH2:59][NH2:60])[CH2:56][CH2:55][O:54][CH2:53]1>CN(C=O)C>[CH2:18]([S:20]([C:23]1[CH:24]=[CH:25][C:26]([O:50][CH3:51])=[C:27]([NH:29][C:30]2[O:31][C:32]([C:35]3[CH:36]=[C:37]([C:41]4[CH:42]=[CH:43][C:44]([C:47]([NH:60][CH2:59][CH2:58][N:57]5[CH2:52][CH2:53][O:54][CH2:55][CH2:56]5)=[O:48])=[CH:45][CH:46]=4)[CH:38]=[CH:39][CH:40]=3)=[CH:33][N:34]=2)[CH:28]=1)(=[O:22])=[O:21])[CH3:19]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 4082852-MorpholinoethylamineHCID 18439658HCID 18439658, compound

Product 1

HCID 10099946HCID 10099946, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In succession, diethylcyanophosphonate (50.0 mg, 0.27 mmol) and triethylamine (65 mg, 0.65 mmol) were added to a solution of the title compound from Example 236 (104.0 mg, 0.22 mmol) and 2-(4-morpholino)ethylamine (54.0 mg, 0.42 mmol) in DMF (2 mL). After the reaction was allowed to stir for 1 h at RT, the reaction was quenched with water (10 mL). The resulting precipitate was filtered, washed with water (10 mL) and dried to afford the title compound (85 mg, 66%) as a tan solid. (In the event that a clean precipitate was not formed on quench, the aqueous solution was washed with 3:1 chloroform/i-propanol (3×20 mL). The combined organic layers were separated, dried by anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure. The crude product purified by chromatography on silica gel using dichloromethane:methanol (up to 20% methanol gradient) as eluent to afford the title compound.) 1H NMR (400 MHz, d6-DMSO): δ 9.71 (bs, 1H), 8.74 (d, J=2.1, 1H), 8.45 (t, J=5.5, 1H), 7.88–7.93 (m, 3H), 7.78 (d, J=8.2, 2H), 7.58–7.64 (m, 3H), 7.52 (t, J=7.7, 1H), 7.44 (dd, J1=2.1, J1=8.5, 1H), 7.23 (d, J=8.6, 1H), 3.93 (s, 3H), 3.52 (t, J=4.5, 4H), 3.36 (q, J=6.4, 2H), 3.25 (s, 2H), 3.15 (q, J=7.3, 2H), 2.33–2.40 (m, 4H), 1.10 (t, J=7.3, 3H). MS (ES+, m/z)=591 (m+H)+.

Workup

  1. customthe reaction was quenched with water (10 mL)
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water (10 mL)
  4. customdried

Sources & evidence

ORD record
ord-552a6ad6a85d421e957fb56e1303c46c
Source dataset
uspto-grants-2007_03
Patent number
US07189712B2

Reaction notes

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