Hydrochloric Acid → HCID 25160469, compound

HRID 558193Notes

Reaction equation

HRID 558193 reaction equation
[Si]([O:8][CH2:9][CH2:10][C:11]1([S:14]([NH:17][C:18]2[C:19]([NH:29][C:30]3[CH:35]=[CH:34][C:33]([I:36])=[CH:32][C:31]=3[F:37])=[C:20]([F:28])[C:21]3[N:25]=[CH:24][N:23]([CH3:26])[C:22]=3[CH:27]=2)(=[O:16])=[O:15])[CH2:13][CH2:12]1)(C(C)(C)C)(C)C.Cl.C(=O)(O)[O-].[Na+]>C1COCC1>[F:28][C:20]1[C:21]2[N:25]=[CH:24][N:23]([CH3:26])[C:22]=2[CH:27]=[C:18]([NH:17][S:14]([C:11]2([CH2:10][CH2:9][OH:8])[CH2:13][CH2:12]2)(=[O:16])=[O:15])[C:19]=1[NH:29][C:30]1[CH:35]=[CH:34][C:33]([I:36])=[CH:32][C:31]=1[F:37]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 59519470HCID 59519470, compound

Product 1

HCID 25160469HCID 25160469, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(2-(Tert-butyldimethylsilyloxy)ethyl)-N-(4-fluoro-5-(2-fluoro-4-iodophenylamino)-1-methyl-1H-benzo[d]imidazol-6-yl)cyclopropane-1-sulfonamide (39 mg, 0.06 mmoles) was dissolved in THF (0.5 ml) and aqueous hydrochloric acid (1.2 N, 0.5 ml) was added at 0° C. After stirring the reaction mixture for two hours, a saturated aqueous solution of sodium bicarbonate (5 ml) was added. The mixture was extracted with EtOAc (3×5 ml). The organic layers were combined, dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by flash chromatography using MeOH/CHCl3 (1/9) yielding to the title compound (27 mg, 83%). m/z=549 [M+1]−.

Workup

  1. extractionThe mixture was extracted with EtOAc (3×5 ml)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-261b1b327d5947ed9669177ce53fefdd
Source dataset
uspto-grants-2011_11
Patent number
US08063049B2

Reaction notes

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