Hydrochloric Acid → HCID 25160596, compound

HRID 1161796Notes

Reaction equation

HRID 1161796 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[O:25][N:24]=[C: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>C1COCC1>[OH: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[O:25][N:24]=[C:23]([CH3:26])[C:22]=3[CH:27]=2)(=[O:16])=[O:15])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59519467HCID 59519467, compound

Product 1

HCID 25160596HCID 25160596, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2-(tert-butyldimethylsilyloxy)ethyl)-N-(7-fluoro-6-(2-fluoro-4-iodophenylamino)-3-methylbenzo[d]isoxazol-5-yl)cyclopropane-1-sulfonamide (20 mg, 0.030 mmol) in THF (2 ml) was added HCl (0.10 ml, 1.2 N in H2O, 0.12 mmol). After stirring for 1 h, the reaction was quenched with saturated aqueous NaHCO3 solution (3 ml) and extracted with EtOAc (2×10 ml). The combined organic solution was dried over Na2SO4 and concentrated. Silica gel chromatography (EtOAc:Hexanes=75:25) yielded 10 mg (61%) of 1-(2-hydroxyethyl)-N-(7-fluoro-6-(2-fluoro-4-iodophenylamino)-3-methylbenzo[d]isoxazol-5-yl)cyclopropane-1-sulfonamide as a white solid. 1H NMR (DMSO-d6, 400 MHz): δ 0.75 (m, 2H), 0.87 (m, 2H), 1.84 (t, J=8 Hz, 2H), 2.57 (s, 3H), 3.38 (m, 2H), 4.52 (s, 1H), 6.59 (m, 1H), 7.34 (d, J=8 Hz, 1H), 7.60 (dd, J=4, 8 Hz, 1H), 7.68 (s, 1H), 7.84 (s, 1H), 9.58 (s, 1H).

Workup

  1. customthe reaction was quenched with saturated aqueous NaHCO3 solution (3 ml)
  2. extractionextracted with EtOAc (2×10 ml)
  3. dry with materialThe combined organic solution was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ae3beda52e0a4de1b0007f113f51e5de
Source dataset
uspto-grants-2010_10
Patent number
US07820664B2

Reaction notes

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