Hydrochloric Acid → HCID 57594555, compound

HRID 1785036Notes

Reaction equation

HRID 1785036 reaction equation
CC([N:5]([C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:21]=[C:22]3[C:27]([CH:28]([OH:30])[CH3:29])=[CH:26][CH:25]=[CH:24][N:23]3[CH:31]=2)=[CH:16][CH:15]=1)[CH2:10][CH2:11][OH:12])[C:6](=[O:8])[O-])(C)C.Cl.O1CCOCC1.C(N(CC)C(C)C)(C)C.[Cl:48][C:49]1[CH:50]=[C:51]([CH:66]=[CH:67][C:68]=1[O:69][CH:70]([CH3:72])[CH3:71])C(OC1C(F)=C(F)C(F)=C(F)C=1F)=O>O>[Cl:48][C:49]1[CH:50]=[C:51]([CH:66]=[CH:67][C:68]=1[O:69][CH:70]([CH3:72])[CH3:71])[C:6]([NH:5][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:21]=[C:22]3[C:27]([CH:28]([OH:30])[CH3:29])=[CH:26][CH:25]=[CH:24][N:23]3[CH:31]=2)=[CH:16][CH:15]=1)[CH2:10][CH2:11][OH:12])=[O:8]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 57594128HCID 57594128, compoundHCID 866088981,1-dimethylethyl[(1S)-3-hydroxy-1-({4-[8-(1-hydroxyethyl)imidazo[1,2-a]pyridin-2-yl]phenyl}methyl)propyl]carbamate

Product 1

HCID 57594555HCID 57594555, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1,1-dimethylethyl[(1S)-3-hydroxy-1-({4-[8-(1-hydroxyethyl)imidazo[1,2-a]pyridin-2-yl]phenyl}methyl)propyl]carbamate (1.08 g, 2.54 mmol) and 4M HCl in 1,4-dioxane (8.0 mL, 32 mmol) was stirred at room temperature for 30 minutes. The reaction was concentrated to dryness redissolved in DMF (25 mL), and to this solution was added N,N-diisopropylethylamine (1.64 g, 12.7 mmol) and pentafluorophenyl 3-chloro-4[(1-methylethyl)oxy]benzoate (0.963 g, 2.54 mmol). The mixture was stirred for 3.0 h at room temperature, diluted with water, and extracted into ethyl acetate. The extracts were washed with water and saturated sodium chloride, dried (Na2SO4), and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (2% MeOH:EtOAc) to give the title compound (0.7 g, 53%) as a pale yellow powder. MS (ES+) m/e 522 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. dissolutionredissolved in DMF (25 mL)
  3. stirringThe mixture was stirred for 3.0 h at room temperature
  4. extractionextracted into ethyl acetate
  5. washThe extracts were washed with water and saturated sodium chloride
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel (2% MeOH:EtOAc)

Sources & evidence

ORD record
ord-fc631dfab8ca41659de32fe1acc8901c
Source dataset
uspto-grants-2009_03
Patent number
US07504413B2

Reaction notes

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