Dimethylformamide → HCID 21074231, compound

HRID 1373182Notes

Reaction equation

HRID 1373182 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([NH2:21])[CH:20]=1)[C:5]([NH:7][C:8]1[N:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=1)=[O:6].[CH3:22][C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](O)=[O:26].CN(C(ON1N=N[C:42]2[CH:43]=[CH:44][CH:45]=N[C:41]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:56](N(C(C)C)CC)(C)[CH3:57].CN([CH:68]=[O:69])C>C(OCC)(=O)C.CCCCCC.O>[CH3:41][C:42]1[CH:57]=[CH:56][CH:45]=[CH:44][C:43]=1[C:68]([NH:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([NH:21][C:25](=[O:26])[C:24]2[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=2[CH3:22])[CH:20]=1)[C:5]([NH:7][C:8]1[N:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=1)=[O:6])=[O:69]

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 83732-Methylbenzoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21074234HCID 21074234, compound

Product 1

HCID 21074231HCID 21074231, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Methyl 6-[(3,5-diaminobenzoyl)amino]-3-pyridinecarboxylate (286 mg, 1 mM) was stirred at room temperature with 2-methylbenzoic acid (248 mg, 1.8 mM), HATU (950 mg, 2.5 mM) and di-isopropylethylamine (1.4 ml, 8 mM) in DMF (20 ml). The mixture was stirred overnight at room temperature and then poured into water and extracted with ethyl acetate. The extracts were dried (magnesium sulphate) filtered and evaporated to give an oil. Chromatography on silica using a gradient of ethyl acetate/hexane to give methyl 6-{[3,5-di-(2-methylbenzoylamino)benzoyl]amino}-3-pyridinecarboxylate (130 mg, 25%); H1 NMR δ (d6-DMSO) 2.5 (6 H s) 3.9 (3 H s) 7.25–7.55 (8 H m) 8.05 (2 H s) 8.3–8.45(3 H mn) 8.9 (1 H s) 10.55 (2 H s) 11.2 (1 H s); MS [MH]+ 523

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extracts were dried (magnesium sulphate)
  3. filtrationfiltered
  4. customevaporated
  5. customto give an oil

Sources & evidence

ORD record
ord-b6af73fb826f4c25a683f5e40808580f
Source dataset
uspto-grants-2007_01
Patent number
US07160906B2

Reaction notes

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