Acetonitrile → HCID 178461069, compound

HRID 746797Notes

Reaction equation

HRID 746797 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Si](Cl)(Cl)(Cl)Cl.C([C:12]1[CH:17]=[C:16]([C:18]([NH2:20])=O)[CH:15]=[CH:14][C:13]=1[C:21]1[CH:26]=[CH:25][C:24]([C:27]2[S:28][CH:29]=[CH:30][C:31]=2[NH:32][S:33]([CH:36]([CH3:38])[CH3:37])(=[O:35])=[O:34])=[CH:23][CH:22]=1)#N.[C:39](#[N:41])C>C(Cl)Cl>[C:39]([C:25]1[CH:26]=[C:21]([C:13]2[CH:14]=[CH:15][C:16]([C:18]3[NH:20][N:3]=[N:2][N:1]=3)=[CH:17][CH:12]=2)[CH:22]=[CH:23][C:24]=1[C:27]1[S:28][CH:29]=[CH:30][C:31]=1[NH:32][S:33]([CH:36]([CH3:38])[CH3:37])(=[O:35])=[O:34])#[N:41]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 24816Silicon tetrachlorideHCID 33557Sodium AzideHCID 69253310HCID 69253310, compound

Product 1

HCID 178461069HCID 178461069, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

Add NaN3 (4.5 mmol) and a 1M solution of SiCl4 (1.5 mmol) in DCM to a solution of 2-Cyano-4′-[3-(propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-4-carboxylic acid amide (1.5 mmol) in acetonitrile (50 mL). Stir 15 h at 70° C. Concentrate to dryness under reduced pressure. Dissolve resultant residue in 20 ml of NH4Cl and extract with DCM and the aqueous with EtOAc. Concentrate all organic layers to dryness. Purify by HPLC to provide the title compound. MS (ES−):449(M−1).

Workup

  1. concentrationConcentrate to dryness under reduced pressure
  2. dissolutionDissolve resultant residue in 20 ml of NH4Cl
  3. extractionextract with DCM
  4. concentrationConcentrate all organic layers to dryness
  5. customPurify by HPLC

Sources & evidence

ORD record
ord-fb6a6c1d36b64063ac532e5c79be5f6c
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Reaction notes

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