3-Amino-9-ethylcarbazole → HCID 86729783, compound

HRID 2272627Notes

Reaction equation

HRID 2272627 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([NH2:16])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].[C:17]([C:19]1[CH:20]=[CH:21][C:22]([NH:25][C:26]([CH2:28][CH:29]([CH3:34])[CH2:30][C:31](O)=[O:32])=[O:27])=[N:23][CH:24]=1)#[N:18].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>CN(C=O)C.O>[C:17]([C:19]1[CH:20]=[CH:21][C:22]([NH:25][C:26](=[O:27])[CH2:28][CH:29]([CH3:34])[CH2:30][C:31]([NH:16][C:12]2[CH:13]=[CH:14][C:15]3[N:3]([CH2:1][CH3:2])[C:4]4[C:9]([C:10]=3[CH:11]=2)=[CH:8][CH:7]=[CH:6][CH:5]=4)=[O:32])=[N:23][CH:24]=1)#[N:18]

Participants

7

Reactant 4

HCID 85883-Amino-9-ethylcarbazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86729782HCID 86729782, compound

Product 1

HCID 86729783HCID 86729783, compoundYield 41.21%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 9-ethyl-9H-carbazol-3-ylamine (306.5 mg, 1.457 mmol) in DMF (7 mL) were added the compound obtained in Step 1 (300 mg, 1.215 mmol), HATU (554.14 mg, 1.457 mmol) and DIPEA (0.632 mL, 3.644 mmol) at room temperature, and the mixture was stirred at room temperature for 16 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate (2×50 mL). The organic layer was dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by preparative HPLC to give the title compound (220 mg, 41.21%) as a colorless powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2×50 mL)
  2. customThe organic layer was dried
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-2d7d2c6684b8453ab194e14ecd12d48b
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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