Ammonia → HCID 66628589, compound

HRID 2201009Notes

Reaction equation

HRID 2201009 reaction equation
[C:1]([C:3]1[C@@H:8]([C:9]2[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=2)[N:7]2[N:17]=[C:18]([S:20](Cl)(=[O:22])=[O:21])[N:19]=[C:6]2[N:5]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)[C:4]=1[CH3:34])#[N:2].N.C([N:38](CC)CC)C>O1CCOCC1>[C:1]([C:3]1[C@@H:8]([C:9]2[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=2)[N:7]2[N:17]=[C:18]([S:20]([NH2:38])(=[O:22])=[O:21])[N:19]=[C:6]2[N:5]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)[C:4]=1[CH3:34])#[N:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8471TriethylamineHCID 86660769HCID 86660769, compound

Product 1

HCID 66628589HCID 66628589, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
7 °C

Procedure

Under an atmosphere of argon, abs. dioxane (5 ml) was stirred with molecular sieve (4 Å, 30 mg) for 30 min. (7R)-6-Cyano-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonyl chloride (63%, 60 mg, 75 μmol) was added and the solution was cooled to 7° C. Dry ammonia gas was then introduced for 15 min, and the mixture was then cooled to 0° C. Triethylamine (11 μl, 75 μmol, 1 eq.) was added, and the reaction was then stirred for 12 h, during which time the mixture gradually warmed to RT. The solvent was then distilled off under reduced pressure, and the residue was purified by preparative HPLC (Reprosil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (33 mg, 90% of theory).

Workup

  1. additionwas added
  2. temperaturethe mixture was then cooled to 0° C
  3. temperaturegradually warmed to RT
  4. distillationThe solvent was then distilled off under reduced pressure
  5. customthe residue was purified by preparative HPLC (Reprosil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA)
  6. customAfter lyophilization, the product was obtained as a solid (33 mg, 90% of theory)

Sources & evidence

ORD record
ord-104c24cbd30a4994beaec0622671f7d0
Source dataset
uspto-grants-2016_06
Patent number
US09359362B2

Reaction notes

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