(Diethylamino)sulfur trifluoride → HCID 117601784, compound

HRID 1773688Notes

Reaction equation

HRID 1773688 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][N:28]=2)(O)[C:9]2[C:17]3[NH:16][C:15](=[O:18])[NH:14][C:13]=3[CH:12]=[C:11]([C:19]3[C:20]([CH3:25])=[N:21][O:22][C:23]=3[CH3:24])[CH:10]=2)=[N:6][CH:7]=1.C(N(S(F)(F)[F:40])CC)C.C([O-])(O)=O.[Na+]>ClCCl>[CH3:25][C:20]1[C:19]([C:11]2[CH:10]=[C:9]([C:8]([F:40])([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][N:28]=3)[C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=3)[C:17]3[NH:16][C:15](=[O:18])[NH:14][C:13]=3[CH:12]=2)=[C:23]([CH3:24])[O:22][N:21]=1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluoride2×HCID 516892Sodium BicarbonateHCID 86296961HCID 86296961, compound

Product 1

HCID 117601784HCID 117601784, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-(bis(5-fluoropyridin-2-yl)(hydroxy)methyl)-6-(3,5-dimethylisoxazol-4-yl)-1H-benzo[d]imidazol-2(3H)-one (10.4 mg, 0.02 mmol) in dichloromethane (2.3 mL) added (diethylamino)sulfur trifluoride (9.15 μl, 0.07 mmol) and stirred for 60 minutes before adding more (diethylamino)sulfur trifluoride (0.01 ml, 0.07 mmol). After 60 minutes from the second addition, the reaction was poured into saturated NaHCO3(aq) (5 mL), the layers were separated, and the aqueous was extracted with dichloromethane (2×5 mL). The combined organics were dried over Na2SO4 and concentrated in vacuo. Purification by reverse-phase HPLC (25-75% acetonitrile/water with 0.01% trifluoroacetic acid, Gemini C18 5μ) afforded 6-(3,5-dimethylisoxazol-4-yl)-4-(fluorobis(5-fluoropyridin-2-yl)methyl)-1H-benzo[d]imidazol-2(3H)-one as an off-white solid.

Workup

  1. additionAfter 60 minutes from the second addition
  2. customthe layers were separated
  3. extractionthe aqueous was extracted with dichloromethane (2×5 mL)
  4. dry with materialThe combined organics were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification by reverse-phase HPLC (25-75% acetonitrile/water with 0.01% trifluoroacetic acid, Gemini C18 5μ)

Sources & evidence

ORD record
ord-4d1d6da39e8442a28c06f22a0f43e060
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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