Water → HCID 86729744, compound

HRID 2272583

Reaction equation

HRID 2272583 reaction equation
[NH2:1][CH2:2][CH:3]([CH3:17])[CH2:4][NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=1)(=[O:8])=[O:7].[CH2:18]([N:20]1[C:32]2[CH:31]=[CH:30][C:29]([C:33](O)=[O:34])=[CH:28][C:27]=2[C:26]2[C:21]1=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH3:19].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.O>CN(C=O)C>[C:15]([C:12]1[CH:11]=[CH:10][C:9]([S:6]([NH:5][CH2:4][CH:3]([CH3:17])[CH2:2][NH:1][C:33]([C:29]2[CH:30]=[CH:31][C:32]3[N:20]([CH2:18][CH3:19])[C:21]4[C:26]([C:27]=3[CH:28]=2)=[CH:25][CH:24]=[CH:23][CH:22]=4)=[O:34])(=[O:8])=[O:7])=[CH:14][CH:13]=1)#[N:16]

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 86729743HCID 86729743, compound

Product 1

HCID 86729744HCID 86729744, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the compound obtained in Step 2 (65.7 mg, 0.26 mmol), 9-ethyl-9H-carbazole-3-carboxylic acid (62.1 mg, 0.26 mmol), HATU (128 mg, 0.34 mmol) and TEA (0.108 mL, 0.78 mmol) in DMF (1.25 mL) was stirred at room temperature for 16 hr. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 50% ethyl acetate/hexane) to give the title compound (81 mg, 0.170 mmol, 65.7%) as a white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5528b8e301bb4cfab9d6adbda426862c
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Linked notes

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