Triethylamine → HCID 178504782, compound

HRID 626682Notes

Reaction equation

HRID 626682 reaction equation
C(N(CC)CC)C.[N:8]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1[CH:17]=O)=[N+:9]=[N-:10].[Cl:19][C:20]1[CH:26]=[C:25]([S:27]([CH3:30])(=[O:29])=[O:28])[CH:24]=[C:23]([Cl:31])[C:21]=1[NH2:22]>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[N:8]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1/[CH:17]=[N:22]/[C:21]1[C:20]([Cl:19])=[CH:26][C:25]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:24][C:23]=1[Cl:31])=[N+:9]=[N-:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 6174182,6-Dichloro-4-mesylanilineHCID 866970374-Azidopyridine-3-carbaldehyde

Product 1

HCID 178504782HCID 178504782, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.7 mL, 12.6 mmol) was added to a cooled (0° C.) mixture of 4-azidopyridine-3-carbaldehyde (621 mg, 4.2 mmol) and 2,6-dichloro-4-(methylsulfonyl)aniline (1 g, 4.2 mmol) in DCM (15 mL) under nitrogen. Titanium tetrachloride (1 M, 2.5 mL, 2.5 mmol) was then added and the resulting mixture was stirred for 1 hour, warmed to room temperature, and stirred for an additional 4 hours. The reaction mixture was concentrated to dryness under reduced pressure. The residue was suspended in toluene and filtered though a pad of Celite®. The filtrate was concentrated to dryness under reduced pressure to afford the title compound as a yellow solid. This crude material was employed in the next step without further purification or analysis.

Workup

  1. temperaturea cooled
  2. stirringstirred for an additional 4 hours
  3. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  4. filtrationfiltered though a pad of Celite®
  5. concentrationThe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-bbad980982144b1d9fb6390e512e61c4
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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