Diisopropylethylamine → HCID 68282460, compound

HRID 513020Notes

Reaction equation

HRID 513020 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([OH:13])=O)=[C:4]2[CH:3]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:47][O:48][C:49]1[CH:65]=[CH:64][C:52]([CH2:53][NH:54][CH2:55][C:56]2[CH:61]=[CH:60][C:59]([O:62][CH3:63])=[CH:58][CH:57]=2)=[CH:51][CH:50]=1>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([N:54]([CH2:53][C:52]3[CH:51]=[CH:50][C:49]([O:48][CH3:47])=[CH:65][CH:64]=3)[CH2:55][C:56]3[CH:57]=[CH:58][C:59]([O:62][CH3:63])=[CH:60][CH:61]=3)=[O:13])=[C:4]2[CH:3]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 714952Bis(4-methoxybenzyl)amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 685073035-Bromopyrazolo[1,5-a]pyridine-3-carboxylic acid

Product 1

HCID 68282460HCID 68282460, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-bromopyrazolo[1,5-a]pyridine-3-carboxylic acid (I-25) (66 mg, 0.27 mmol) in DMF (3 mL) was added DIEA (0.14 mL) and HATU (0.10 g, 0.27 mmol). The reaction was stirred for 30 minutes at room temperature then bis(4-methoxybenzyl)amine (70 mg, 0.27 mmol) was added. Stirring was continued at room temperature for 12 hours. The reaction was diluted with EtOAc, washed with brine, dried over magnesium sulfate, filtered and reduced to dryness. The crude product was purified by flash column chromatography on silica with hexanes/EtOAc gradient as eluant to yield 5-bromo-N,N-bis(4-methoxybenzyl)pyrazolo[1,5-a]pyridine-3-carboxamide (I-26). 1H NMR (400 MHz, CDCl3) δ 8.50 (d, J=2.4 Hz, 1 H), 8.26 (dd, J=0.4, 7.2 Hz, 1 H), 7.88 (s, 1 H), 7.22 (d, J=8.0 Hz, 4 H), 7.00 (dd, J=2.0, 7.2 Hz, 1 H), 6.91 (d, J=8.4 Hz, 4 H), 4.67 (s, 4 H), 3.82 (s, 6 H). MS m/z 480.1, 482.1 (M+1)+.

Workup

  1. stirringStirring
  2. waitwas continued at room temperature for 12 hours
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customThe crude product was purified by flash column chromatography on silica with hexanes/EtOAc gradient as eluant

Sources & evidence

ORD record
ord-f1b7d6d23d1844ac92159804db9ae8f8
Source dataset
uspto-grants-2015_08
Patent number
US09102671B2

Reaction notes

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