Hydrochloric Acid → HCID 86729762, compound

HRID 2272605Notes

Reaction equation

HRID 2272605 reaction equation
[NH2:1][CH:2]([CH3:22])[C:3]([NH:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]2[N:11]([CH2:20][CH3:21])[C:12]3[C:17]([C:18]=2[CH:19]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:4].[C:23]([C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32](O)=[O:33])=[CH:27][CH:26]=1)#[N:24].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl>CN(C=O)C>[C:23]([C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32]([NH:1][C@H:2]([C:3]([NH:5][CH2:6][C:7]2[CH:8]=[CH:9][C:10]3[N:11]([CH2:20][CH3:21])[C:12]4[C:17]([C:18]=3[CH:19]=2)=[CH:16][CH:15]=[CH:14][CH:13]=4)=[O:4])[CH3:22])=[O:33])=[CH:27][CH:26]=1)#[N:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 795874-Cyanophenylacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86729761HCID 86729761, compound

Product 1

HCID 86729762HCID 86729762, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the compound obtained in Step 2 (242 mg, 0.82 mmol), 2-(4-cyanophenyl)acetic acid (198 mg, 1.23 mmol), HATU (468 mg, 1.23 mmol) and TEA (0.343 mL, 2.46 mmol) in DMF (3 mL) was stirred at room temperature for 16 hr. To the reaction solution was added dilute hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent: ethyl acetate) to give the title compound (50.3 mg, 0.115 mmol, 14%) as a white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with dilute hydrochloric acid
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent: ethyl acetate)

Sources & evidence

ORD record
ord-885e29db0a0940aaa1d035ef79a6000d
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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