Diisopropylethylamine → HCID 86761199, compound

HRID 1161649Notes

Reaction equation

HRID 1161649 reaction equation
Cl.Cl.[CH:3]12[CH2:14][CH:10]([CH2:11][NH:12][CH2:13]1)[C:9]1[CH:8]=[CH:7][C:6]([NH:15][C:16]3[N:21]=[C:20](NC4CC4)[C:19]([C:26]([F:29])([F:28])[F:27])=[CH:18][N:17]=3)=[CH:5][C:4]2=1.CCN([CH:36]([CH3:38])[CH3:37])C(C)C.Cl.[C:40](Cl)(=[O:47])[C:41]1[CH:46]=[CH:45][CH:44]=[N:43][CH:42]=1>O1CCOCC1>[CH:36]1([C:20]2[C:19]([C:26]([F:28])([F:29])[F:27])=[CH:18][N:17]=[C:16]([NH:15][C:6]3[CH:7]=[CH:8][C:9]4[CH:10]5[CH2:14][CH:3]([CH2:13][N:12]([C:40]([C:41]6[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=6)=[O:47])[CH2:11]5)[C:4]=4[CH:5]=3)[N:21]=2)[CH2:38][CH2:37]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 68692475HCID 68692475, compound

Product 1

HCID 86761199HCID 86761199, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 13 (200 mg, 446 μmol) and DIEA (124 μL, 880 μmol) in 1,4-dioxane (2 mL) was treated with in one portion with nicotinoyl chloride hydrochloride (80 mg, 446 μmol). The mixture was stirred at room temperature for 4 hours and concentrated under reduced pressure. The resultant residue was purified on silica (3% CH3OH/CH2Cl2) to provide 15 as an off-white solid (52 mg, 20% yield). HPLC Rt 5.7 minutes; LC/MS (Method F) m/z 427 (MH+).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe resultant residue was purified on silica (3% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-36f47d29696c495c81fea6c701d58844
Source dataset
uspto-grants-2010_10
Patent number
US07820648B2

Reaction notes

Loading…