Acetyl chloride → HCID 67294556, compound

HRID 518006Notes

Reaction equation

HRID 518006 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[C:15]([C:17]#[N:18])[C:14]3[N:19]=[N:20][N:21]([CH3:22])[C:13]=3[CH:12]=2)=[CH:7][C:6]=1[C:23]([F:26])([F:25])[F:24].CCN(C(C)C)C(C)C.[C:36](Cl)(=[O:38])[CH3:37]>C1COCC1.C(Cl)Cl>[C:17]([C:15]1[C:14]2[N:19]=[N:20][N:21]([CH3:22])[C:13]=2[CH:12]=[C:11]([C:8]2[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][NH:1][C:36](=[O:38])[CH3:37])=[C:6]([C:23]([F:25])([F:24])[F:26])[CH:7]=2)[N:16]=1)#[N:18]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 67294688HCID 67294688, compound

Product 1

HCID 67294556HCID 67294556, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

6-(4-(2-Aminoethoxy)-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo-[4,5-c]pyridine-4-carbonitrile (0.276 mmol, 0.1 g) and Hunig's base (0.828 mmol, 0.137 ml, 0.107 g) were stirred in THF (1 ml) at 0° C. acetyl chloride (0.552 mmol, 0.039 ml, 0.043 g) was added and the reaction was allowed to warm to room temperature and stirred for 1 hour. The resulting residue was taken up in DCM and washed with water. The organic was concentrated at reduced pressure. The resulting residue was purified by silica chromatography, eluting with DCM—3% MeOH/DCM to afford N-(2-(4-(4-cyano-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)phenoxy)ethyl)acetamide. (0.024 g)

Workup

  1. additionwas added
  2. washwashed with water
  3. concentrationThe organic was concentrated at reduced pressure
  4. customThe resulting residue was purified by silica chromatography
  5. washeluting with DCM—3% MeOH/DCM

Sources & evidence

ORD record
ord-5f6dfed0b6004bfab411afbd6d97739e
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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