Hydrochloric Acid → HCID 86729745, compound

HRID 2272585Notes

Reaction equation

HRID 2272585 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:17])[CH2:11][S:12][CH2:13][C:14]([OH:16])=O)=[CH:5][CH:4]=1)#[N:2].[CH2:18]([N:20]1[C:32]2[CH:31]=[CH:30][C:29]([NH2:33])=[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.CCN(C(C)C)C(C)C.Cl>CN(C=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:17])[CH2:11][S:12][CH2:13][C:14]([NH: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:16])=[CH:7][CH:8]=1)#[N:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 85883-Amino-9-ethylcarbazoleHCID 81531DiisopropylethylamineHCID 2812223HCID 2812223, compoundHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 86729745HCID 86729745, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the compound obtained in Step 1 (145 mg, 0.58 mmol), 9-ethyl-9H-carbazol-3-amine (122 mg, 0.58 mmol), HATU (330 mg, 0.87 mmol) and DIEA (225 mg, 1.74 mmol) in DMF (4 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 to give the title compound (150 mg, 0.339 mmol, 59%) 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

Sources & evidence

ORD record
ord-9bdcbdd3da0f40cd92a4428eed8bf51f
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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