Acetyl chloride → HCID 53330391, compound

HRID 517988Notes

Reaction equation

HRID 517988 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[C:20]([C:22]#[N:23])[C:19]3[N:24]=[N:25][N:26]([CH3:27])[C:18]=3[CH:17]=2)=[CH:12][C:11]=1[C:28]([F:31])([F:30])[F:29].C(N(CC)CC)C>C(Cl)Cl.O>[C:22]([C:20]1[C:19]2[N:24]=[N:25][N:26]([CH3:27])[C:18]=2[CH:17]=[C:16]([C:13]2[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH2:7][CH2:6][NH:5][C:1](=[O:3])[CH3:2])=[C:11]([C:28]([F:30])([F:29])[F:31])[CH:12]=2)[N:21]=1)#[N:23]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 67294188HCID 67294188, compound

Product 1

HCID 53330391HCID 53330391, compoundYield 4.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (18.3 mg) was added to a mixture of 6-(4-(3-aminopropoxy)-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile (100 mg) and triethylamine (294 μl) in DCM (2 ml). The mixture was stirred at room temperature for 2 hours then diluted with water, the organic layer was separated, dried over magnesium sulphate, and solvent was removed under reduced pressure. The residue was purified by HPLC to give the expected product (4.4 mg). 1H NMR (CD3OD) δ: 8.56 (s, 1H), 8.38-8.45 (m, 2H), 7.33 (d, 1H), 4.45 (s, 3H), 4.23 (t, 2H), 3.40 (t, 2H), 2.05 (quin, 2H), 1.95 (s, 3H). MS m/z 419 (M+H).

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over magnesium sulphate, and solvent
  3. customwas removed under reduced pressure
  4. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-32d1ed1e50a84483abfe60cbd0beb0bf
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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