Triethylamine → HCID 66682146, compound

HRID 530309Notes

Reaction equation

HRID 530309 reaction equation
FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.[CH3:15][N:16]([CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)[C:17]([N:19]1[CH:23]=[C:22]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[N:21]=[CH:20]1)=[O:18].C(N(CC)CC)C.[CH3:43][S:44](Cl)(=[O:46])=[O:45]>ClCCl.CN(C1C=CN=CC=1)C>[CH3:15][N:16]([CH:30]1[CH2:35][CH2:34][N:33]([S:44]([CH3:43])(=[O:46])=[O:45])[CH2:32][CH2:31]1)[C:17]([N:19]1[CH:23]=[C:22]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[N:21]=[CH:20]1)=[O:18]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86663117HCID 86663117, compound

Product 1

HCID 66682146HCID 66682146, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To an ice-water cooled suspension of N-methyl-N-(piperidin-4-yl)-4-(pyridin-3-yl)-1H-imidazole-1-carboxamide bis(2,2,2-trifluoroacetate) (300 mg, 0.584 mmol) in dichloromethane (10 mL) was added DMAP (35.7 mg, 0.292 mmol), followed by the dropwise addition of triethylamine (0.326 mL, 2.337 mmol), followed in turn by addition of methanesulfonyl chloride (0.072 mL, 0.934 mmol). The solution was allowed to stir at room temperature overnight, whereupon it was quenched by the addition of methanol and allowed to stir at room temperature. The white precipitate was collected by filtration, washed with methanol and ether, then dried to give the product as a white solid, (158 mg, 74%).

Workup

  1. customwas quenched by the addition of methanol
  2. stirringto stir at room temperature
  3. filtrationThe white precipitate was collected by filtration
  4. washwashed with methanol and ether
  5. customdried

Sources & evidence

ORD record
ord-0bbd781d8aa848c4a3ea4ec480081540
Source dataset
uspto-grants-2016_05
Patent number
US09353082B2

Reaction notes

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