Diisopropylethylamine → HCID 56962057, compound

HRID 1958207Notes

Reaction equation

HRID 1958207 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([NH:20][C:21]([C:23]3[CH:24]=[N:25][CH:26]=[C:27]([CH:31]=3)[C:28](O)=[O:29])=[O:22])[CH:11]=[N:12][C:13]=2[O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:4][CH:3]=1.Cl.CN.[CH3:35][N:36](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([NH:20][C:21]([C:23]3[CH:24]=[N:25][CH:26]=[C:27]([C:28]([NH:36][CH3:35])=[O:29])[CH:31]=3)=[O:22])[CH:11]=[N:12][C:13]=2[O:14][CH2:15][C:16]([F:18])([F:17])[F:19])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 6364545Methylamine hydrochlorideHCID 67280524HCID 67280524, compound

Product 1

HCID 56962057HCID 56962057, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-[5-(4-Chloro-phenyl)-6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylcarbamoyl]-nicotinic acid (120 mg, 260 μmol) and methylamine hydrochloride (140 mg, 2.6 mmol) were dissolved in DMF (3 mL). TBTU (125 mg, 390 μmol) and DIPEA (672 mg, 908 μl, 5.2 mmol) were added. The reaction mixture was stirred at room temperature for 20 h. The crude reaction mixture was concentrated in vacuo and purified by flash chromatography (silica gel, 10 g, 0% to 100% ethyl acetate in heptane) to deliver 34 mg (28%) of the title compound as white solid; LC-MS (UV peak area/ESI) 99.5%, 465.0928 (M+H)+.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated in vacuo
  3. custompurified by flash chromatography (silica gel, 10 g, 0% to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-4dd8c4699fab4f22be71bc407100356c
Source dataset
uspto-grants-2013_04
Patent number
US08410107B2

Reaction notes

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