Hydrochloric Acid → N-(7-chloro-6-(2-fluoro-4-iodophenylamino)-3-methyl-3a,7a-dihydro-3H-imidazo[4,5-b]pyridin-5-yl)-1-(2-hydroxyethyl)cyclopropane-1-sulfonamide

HRID 558222Notes

Reaction equation

HRID 558222 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]([Cl:28])[CH:21]3[N:26]=[CH:25][N:24]([CH3:27])[CH:22]3[N:23]=2)(=[O:16])=[O:15])[CH2:13][CH2:12]1)(C(C)(C)C)(C)C.Cl>C1COCC1>[Cl:28][C:20]1[CH:21]2[N:26]=[CH:25][N:24]([CH3:27])[CH:22]2[N:23]=[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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 669994361-(2-(tert-butyldimethylsilyloxy)ethyl)-N-(7-chloro-6-(2-fluoro-4-iodophenylamino)-3-methyl-3a,7a-dihydro-3H-imidazo[4,5-b]pyridin-5-yl)cyclopropane-1-sulfonamide

Product 1

HCID 66999500N-(7-chloro-6-(2-fluoro-4-iodophenylamino)-3-methyl-3a,7a-dihydro-3H-imidazo[4,5-b]pyridin-5-yl)-1-(2-hydroxyethyl)cyclopropane-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2-(tert-butyldimethylsilyloxy)ethyl)-N-(7-chloro-6-(2-fluoro-4-iodophenylamino)-3-methyl-3a,7a-dihydro-3H-imidazo[4,5-b]pyridin-5-yl)cyclopropane-1-sulfonamide (40 mg, 0.060 mmol) in THF (2 ml) is added HCl (0.20 ml, 1.2 N in H2O, 0.24 mmol). After stirring for 1 h, the reaction is quenched with saturated aqueous NaHCO3 solution (3 ml) and extracted with EtOAc (2×10 ml). The combined organic solution is dried over Na2SO4 and concentrated. Silica gel chromatography yields the title compound.

Workup

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

Sources & evidence

ORD record
ord-2e03c9cf56e44386b422cd8985d83a15
Source dataset
uspto-grants-2011_11
Patent number
US08063049B2

Reaction notes

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