Ammonium Chloride → HCID 178478060, compound

HRID 2401839Notes

Reaction equation

HRID 2401839 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][C:7]2[N:8]=[C:9]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[S:10][C:11]=2[C:12]#[N:13])=[CH:4][CH:3]=1.[N-:22]=[N+:23]=[N-:24].[Na+].[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[N:8]=[C:9]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[S:10][C:11]=2[C:12]2[NH:24][N:23]=[N:22][N:13]=2)=[CH:20][CH:21]=1

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 66747914HCID 66747914, compound

Product 1

HCID 178478060HCID 178478060, compoundYield 5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution 4-(4-chlorobenzyl)-2-(pyridin-4-yl)thiazole-5-carbonitrile (167 mg, 0.536 mmol) in DMF (3.5 mL) was added sodium azide (104 mg, 1.61 mmol) and ammonium chloride (86 mg, 1.61 mmol) and the resulting mixture was heated at 100 degrees overnight. The reaction was cooled and taken up in ethyl acetate and water. The aqueous layer was concentrated in vacuo, and the residue was purified by silica gel chromatography (MeOH/DCM=0/100→10/90) to give 9 mg (5% yield) of the title compound. LC/MS (FA) ES+ 355, 357. 1H NMR (400 MHz, DMSO-d6) δ: 8.74-8.73 (m, 2H), 7.93-7.92 (m, 2H), 7.38-7.32 (m, 4H), 4.62 (s, 2H).

Workup

  1. temperaturethe resulting mixture was heated at 100 degrees overnight
  2. temperatureThe reaction was cooled
  3. concentrationThe aqueous layer was concentrated in vacuo
  4. customthe residue was purified by silica gel chromatography (MeOH/DCM=0/100→10/90)

Sources & evidence

ORD record
ord-07ea4859ce664d2a96879d5c751b08db
Source dataset
uspto-grants-2014_08
Patent number
US08796268B2

Reaction notes

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