Triethylamine → HCID 66818426, compound

HRID 1024672Notes

Reaction equation

HRID 1024672 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][C:13]1[C:14]([O:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]#[N:36])=[CH:31][CH:30]=2)=[N:15][C:16]([O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=2)=[CH:17][CH:18]=1.C(N(CC)CC)C.C(N(CC)C(C)C)(C)C>O1CCCC1>[C:35]([C:32]1[CH:33]=[CH:34][C:29]([O:28][C:14]2[C:13]([NH:12][S:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)(=[O:10])=[O:9])=[CH:18][CH:17]=[C:16]([O:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=3)[N:15]=2)=[CH:30][CH:31]=1)#[N:36]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 66818531HCID 66818531, compound

Product 1

HCID 66818426HCID 66818426, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Fluoro benzene sulfonyl chloride (0.15 g, 0.77 mmol), dissolved in 2 ml of tetrahydrofuran (THF), was added to a stirred solution of 3-amino-2,6-bis(4-cyano phenoxy)pyridine (0.25 g, 0.77 mmol), triethylamine (0.155 g, 1.54 mmol) and N,N-diisopropylethylamine (0.1 g, 0.77 mmol), in 10 ml of THF, in an inert atmosphere and stirred at RT for 12 h. The reaction mixture was concentrated and dissolved in 100 ml of ethyl acetate, washed with 1 N HCl followed by saturated brine solution and dried over anhydrous sodium sulphate. The organic phase was concentrated and the crude product was purified by column chromatography to afford 0.3 g of the required compound. 1H NMR (DMSO-d6): δ 6.94 (1H, d), 7.12 (2H, m), 7.25 (1H, d), 7.35 (4H, d), 7.56 (4H, m), 7.80 (4H, m), 8.04 (4H, m).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in 100 ml of ethyl acetate
  3. washwashed with 1 N HCl
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationThe organic phase was concentrated
  6. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-3279b4fbfe1a44c390ceb2a5ceb7553b
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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