Sulfuryl chloride → HCID 57812309, compound

HRID 912004Notes

Reaction equation

HRID 912004 reaction equation
[N-]=[C:2]=O.S(Cl)(Cl)(=O)=O.Cl.Cl.[Cl:11][C:12]1[C:17]([F:18])=[CH:16][CH:15]=[C:14]([Cl:19])[C:13]=1[C@H:20]([O:22][C:23]1[C:24]2[O:32][CH:31]=[C:30]([C:33]3[CH:34]=[N:35][N:36]([CH:38]4[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]4)[CH:37]=3)[C:25]=2[CH:26]=[N:27][C:28]=1[NH2:29])[CH3:21].CCN([CH:50]([CH3:52])[CH3:51])C(C)C.Cl[C:54]([O-:56])=[O:55]>CN(C=O)C.[N-]=C=O>[NH2:29][C:28]1[N:27]=[CH:26][C:25]2[C:30]([C:33]3[CH:34]=[N:35][N:36]([CH:38]4[CH2:39][CH2:40][N:41]([C:54]([O:56][C:50]([CH3:52])([CH3:2])[CH3:51])=[O:55])[CH2:42][CH2:43]4)[CH:37]=3)=[CH:31][O:32][C:24]=2[C:23]=1[O:22][C@@H:20]([C:13]1[C:14]([Cl:19])=[CH:15][CH:16]=[C:17]([F:18])[C:12]=1[Cl:11])[CH3:21]

Participants

8

Reactant 5

HCID 24648Sulfuryl chloride2×HCID 81531DiisopropylethylamineHCID 105034IsocyanateHCID 21226386Carbonochloridate2×HCID 67401992HCID 67401992, compound

Product 1

HCID 57812309HCID 57812309, compound

Reagents, catalysts & solvents 2

HCID 105034IsocyanateCatalystHCID 6228DimethylformamideSolvent2×

Procedure

General procedure Q for N-alkylation/acylation, using isocyanate, chloroformate, and sulfonyl chloride species: To a solution of 7-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-3-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]furo[3,2-c]pyridin-6-amine dihydrochloride (10.6 mg, 0.0188 mmol, 1 eq) and DIPEA (26 μL, 0.15 mmol, 8 eq) in DMF (1 mL), one drop of the isocyanate, chloroformate, or sulfonyl chloride (approx. 0.0346 mmol, 1.8 eq) was added and the reaction was stirred at rt for 1 h. The DMF solution was syringe filtered and submitted directly to the analytical department for purification by MDPS. Fractions containing product were pooled together and all solvent was removed using the SpeedVac to give the title material.

Workup

  1. filtrationfiltered
  2. customsubmitted directly to the analytical department for purification by MDPS
  3. additionFractions containing product
  4. customall solvent was removed

Sources & evidence

ORD record
ord-800a723f154943c6bc0be9168f22aa91
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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