Hydrochloric Acid → HCID 57636928, compound

HRID 15975Notes

Reaction equation

HRID 15975 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:10]([CH3:32])[C:11](=[O:31])[C:12]([CH3:30])=[CH:13][C:14]=2[C:15]([NH:17][O:18][CH2:19][C@@H:20]([O:22][Si](C(C)(C)C)(C)C)[CH3:21])=[O:16])=[C:4]([F:33])[CH:3]=1.Cl>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:10]([CH3:32])[C:11](=[O:31])[C:12]([CH3:30])=[CH:13][C:14]=2[C:15]([NH:17][O:18][CH2:19][C@@H:20]([OH:22])[CH3:21])=[O:16])=[C:4]([F:33])[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86624668(S)-2-(4-bromo-2-fluorophenylamino)-N-(2-(tert-butyldimethylsilyloxy)propoxy)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Product 1

HCID 57636928HCID 57636928, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-2-(4-bromo-2-fluorophenylamino)-N-(2-(tert-butyldimethylsilyloxy)propoxy)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxamide (0.037 g, 0.0682 mmol) in THF (1.00 mL) was added 1 M HCl (0.682 mL, 0.682 mmol). The reaction mixture was stirred for one hour at room temperature. The reaction mixture was diluted with EtOAc and washed with saturated NaHCO3 (3×), saturated NaCl (1×), dried (Na2SO4), and concentrated under reduced pressure. Purification by flash column chromatography (methylene chloride/methanol, 30:1) gave 0.020 (69%) pure desired product as a yellow solid. MS ESI (+) m/z 428, 430 (M+, Br pattern) detected; 1H NMR (400 MHz, CD3OD) δ 7.55 (s, 1H), 7.40 (d, 1H), 7.24 (d, 1H), 6.68 (t, 1H), 3.86 (m, 1H), 3.71 (m, 1H), 3.58 (m, 1H), 3.40 (s, 3H), 2.12 (s, 3H), 1.10 (d, 3H).

Workup

  1. washwashed with saturated NaHCO3 (3×), saturated NaCl (1×)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customPurification by flash column chromatography (methylene chloride/methanol, 30:1)

Sources & evidence

ORD record
ord-fed27da4679b47c4beedd62445fe70e8
Source dataset
uspto-grants-2010_06
Patent number
US07732616B2

Reaction notes

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