Triethylamine → HCID 117701039, compound

HRID 1845888Notes

Reaction equation

HRID 1845888 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([O:12][C:13]1[C:14]([NH2:30])=[N:15][CH:16]=[C:17]([C:19]2[N:20]=[N:21][N:22]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[CH:23]=2)[CH:18]=1)[CH3:11].C(N(CC)CC)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>CN(C)C=O>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([O:12][C:13]1[C:14]([NH2:30])=[N:15][CH:16]=[C:17]([C:19]2[N:20]=[N:21][N:22]([CH:24]3[CH2:29][CH2:28][N:27]([S:39]([CH3:38])(=[O:41])=[O:40])[CH2:26][CH2:25]3)[CH:23]=2)[CH:18]=1)[CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 71621328HCID 71621328, compound

Product 1

HCID 117701039HCID 117701039, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product of the above mentioned Example 2 3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1-(piperidin-4-yl)-1H-1,2,3-triazol-4-yl)-2-aminopyridine (451 mg, 1 mmol) was added to N,N-dimethyl formamide (10 mL), triethylamine (404 mg, 4 mmol) and methylsulfonyl chloride (343.6 mg, 3 mmol) were added, and the reaction was performed overnight at room temperature. The resultant mixture was washed with water for several times, dried over anhydrous sodium sulfate, filtered, the filtrate was rotatedly concentrated to dryness to yield a solid, which was purified via silica gel column chromatography (dichloromethane/methanol=20:1) to yield the target product as white solid powder.

Workup

  1. additionwere added
  2. washThe resultant mixture was washed with water for several times
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was rotatedly concentrated to dryness
  6. customto yield a solid, which
  7. customwas purified via silica gel column chromatography (dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-f5fae67753214beebe619ea58df83888
Source dataset
uspto-grants-2015_02
Patent number
US08952002B2

Reaction notes

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