Triethylamine → HCID 22291587, compound

HRID 457305Notes

Reaction equation

HRID 457305 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([Cl:11])=[CH:9][N:10]=1)[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[NH2:43][C:44]1[CH:68]=[CH:67][C:47]2[CH2:48][CH2:49][C:50]3[C:51]([C:64]([NH2:66])=[O:65])=[N:52][N:53]([C:55]4[CH:63]=[CH:62][C:58]5[O:59][CH2:60][O:61][C:57]=5[CH:56]=4)[C:54]=3[C:46]=2[CH:45]=1>CN(C=O)C>[O:59]1[C:58]2[CH:62]=[CH:63][C:55]([N:53]3[C:54]4[C:46]5[CH:45]=[C:44]([NH:43][C:5](=[O:7])[C:4]6[C:8]([Cl:11])=[CH:9][N:10]=[C:2]([Cl:1])[CH:3]=6)[CH:68]=[CH:67][C:47]=5[CH2:48][CH2:49][C:50]=4[C:51]([C:64]([NH2:66])=[O:65])=[N:52]3)=[CH:56][C:57]=2[O:61][CH2:60]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27360872,5-Dichloroisonicotinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22291565HCID 22291565, compound2×

Product 1

HCID 22291587HCID 22291587, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,5-Dichloroisonicotinic acid (1.65 g, 0.0086 mol), HATU (3.27 g, 0.0086 mol) and finally Et3N (2.32 mL, 0.0166 mol) were added to a solution of the title compound of step 4 of Example 161 (2 g, 0.00574 mol) in 29 mL of DMF. The reaction mixture was stirred at room temperature for 3 h. The completion of the reaction was confirmed by monitoring the disappearance of the title compound of step 4 of Example 161 in LC/MS. The crude reaction mixture was concentrated to about 10 mL of DMF. Upon addition of water to this DMF residue, a white solid was formed. This white solid was triturated in water for 20 min and filtered. The solid was collected, dissolved in THF, and dried with MgSO4. Removal of the solvent afforded a brown solid that was triturated in warm CH3CN (80° C.) to give 2.2 g of the title compound (yield 73%). Mp: 292–293° C. 1H NMR (300 MHz, d6-DMSO): δ 2.90–2.92 (m, 4H), 6.09 (s, 2H), 6.94–7.04 (m, 2H), 7.12 (d, 1H, J=2 Hz), 7.26–7.38 (m, 4H), 7.51 (s, 1H), 7.81 (s, 1H), 8.61 (s, 1H), 10.54 (s, 1H). M+1=523.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated to about 10 mL of DMF
  3. additionUpon addition of water to this DMF residue
  4. customa white solid was formed
  5. customThis white solid was triturated in water for 20 min
  6. filtrationfiltered
  7. customThe solid was collected
  8. dissolutiondissolved in THF
  9. dry with materialdried with MgSO4
  10. customRemoval of the solvent
  11. customafforded a brown solid that
  12. customwas triturated in warm CH3CN (80° C.)

Sources & evidence

ORD record
ord-442213ab24a240efb0a703bc32e6072d
Source dataset
uspto-grants-2007_03
Patent number
US07186743B2

Reaction notes

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