Diisopropylethylamine → HCID 11647352, compound

HRID 735794Notes

Reaction equation

HRID 735794 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH:4]=[C:3]1[C:18]([OH:20])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:45][C:46]1[C:47](=[O:56])[NH:48][CH:49]=[C:50]([C:52]([CH3:55])([CH3:54])[CH3:53])[CH:51]=1.C(N(CC)C(C)C)(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[C:52]([C:50]1[CH:51]=[C:46]([NH:45][C:18]([C:3]2[N:2]([CH3:1])[C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][C:9]=3[O:11][C:12]2[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=2)=[O:20])[C:47](=[O:56])[NH:48][CH:49]=1)([CH3:55])([CH3:53])[CH3:54]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22025245HCID 22025245, compoundHCID 58980663HCID 58980663, compound

Product 1

HCID 11647352HCID 11647352, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Methyl-7-(pyridine-4-yloxy)-1H-indole-2-carboxylic acid (145 mg, 0.542 mmol) and HATU (206 mg, 0.542 mmol) were combined in DMF (1 mL) and stirred 5 min at room temperature. The above aminopyridinone (90 mg, 0.542 mmol) was added to the reaction mixture followed by N,N-diisopropylethylamine (283 microL, 1.63 mmol). The solution was stirred at room temperature for 72 h then poured into saturated aqueous NaHCO3. The aqueous layer was extracted with chloroform and the combined extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. Purification by silica-gel chromatography (2% ammonium hydroxide, 50% ethyl acetate in hexane) provided 1-methyl-7-(pyridine-4-yloxy)-1H-indole-2-carboxylic acid (5-tert-butyl-2-oxo-1,2-dihydropyridin-3-yl)-amide (163 mg, 73%) as a white solid: mp: 236-238° C. (dec.); ESI MS m/z 417 [C24H24N4O3+H]+; HPLC>97%, tR=14.74 min.

Workup

  1. stirringThe solution was stirred at room temperature for 72 h
  2. extractionThe aqueous layer was extracted with chloroform
  3. dry with materialthe combined extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica-gel chromatography (2% ammonium hydroxide, 50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-1ad63052eb144d19ac512981884e85a7
Source dataset
uspto-grants-2009_09
Patent number
US07592332B2

Reaction notes

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