Water → HCID 86729757, compound

HRID 2272599Notes

Reaction equation

HRID 2272599 reaction equation
[NH2:1][CH2:2][CH:3]([CH3:16])[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=1)=[O:5].[CH2:17]([N:19]1[C:31]2[CH:30]=[CH:29][C:28]([C:32](O)=[O:33])=[CH:27][C:26]=2[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH3:18].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.O>CN(C=O)C>[C:14]([C:11]1[CH:10]=[CH:9][C:8]([CH2:7][NH:6][C:4](=[O:5])[CH:3]([CH3:16])[CH2:2][NH:1][C:32]([C:28]2[CH:29]=[CH:30][C:31]3[N:19]([CH2:17][CH3:18])[C:20]4[C:25]([C:26]=3[CH:27]=2)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[O:33])=[CH:13][CH:12]=1)#[N:15]

Participants

6

Reactant 4

HCID 962WaterHCID 49128699-Ethyl-9H-carbazole-3-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 62671211HCID 62671211, compound

Product 1

HCID 86729757HCID 86729757, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution (2.5 mL) of the compound obtained in Step 2 (112 mg, 0.52 mmol), 9-ethyl-9H-carbazole-3-carboxylic acid (123 mg, 0.52 mmol), HATU (255 mg, 0.67 mmol) and TEA (0.216 mL, 1.55 mmol) in DMF was stirred at room temperature for 16 hr. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was 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 (158 mg, 0.360 mmol, 69.9%) as a white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic layer was dried
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (solvent; ethyl acetate)

Sources & evidence

ORD record
ord-532f0ed132004cb7a4ba8d88c0851ef5
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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