Hydrochloric Acid → HCID 57594292, compound

HRID 222885Notes

Reaction equation

HRID 222885 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C@@H:13]([NH:33][C:34](=[O:40])OC(C)(C)C)[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:22]=[C:23]3[C:28]([CH:29]([OH:31])[CH3:30])=[CH:27][CH:26]=[CH:25][N:24]3[CH:32]=2)=[CH:17][CH:16]=1.Cl.O1CCOCC1.C(N(CC)C(C)C)(C)C.[Cl:57][C:58]1[CH:59]=[C:60]([CH:75]=[CH:76][C:77]=1[O:78][CH:79]([CH3:81])[CH3:80])C(OC1C(F)=C(F)C(F)=C(F)C=1F)=O>O>[Cl:57][C:58]1[CH:59]=[C:60]([CH:75]=[CH:76][C:77]=1[O:78][CH:79]([CH3:81])[CH3:80])[C:34]([NH:33][C@@H:13]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:22]=[C:23]3[C:28]([CH:29]([OH:31])[CH3:30])=[CH:27][CH:26]=[CH:25][N:24]3[CH:32]=2)=[CH:17][CH:16]=1)[CH2:12][N:3]1[C:2](=[O:1])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]1=[O:11])=[O:40]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 57594128HCID 57594128, compoundHCID 575943381,1-Dimethylethyl [(1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-({4-[8-(1-hydroxyethyl)imidazo[1,2-a]pyridin-2-yl]phenyl}methyl)ethyl]carbamate

Product 1

HCID 57594292HCID 57594292, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1,1-dimethylethyl [(1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-({4-[8-(1-hydroxyethyl)imidazo[1,2-a]pyridin-2-yl]phenyl}methyl)ethyl]carbamate (1.79 g, 3.31 mmol) and 4 M HCl in 1,4-dioxane (20 mL, 80 mmol) was stirred at room temperature for 45 minutes. The reaction was concentrated to dryness and redissolved in DMF (30 mL). To this solution was added N,N-diisopropylethylamine (2.14 g, 16.55 mmol) and pentafluorophenyl 3-chloro-4[(1-methylethyl)oxy]benzoate (1.36 g, 3.31 mmol). The mixture was stirred overnight at room temperature, diluted with water, and extracted into ethyl acetate. The extracts were washed with water, dried (Na2SO4), and concentrated in vacuo to give the title compound (2.10 g, 100%) as a tan solid. MS (ES+) m/e 637 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. dissolutionredissolved in DMF (30 mL)
  3. stirringThe mixture was stirred overnight at room temperature
  4. extractionextracted into ethyl acetate
  5. washThe extracts were washed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-38ec0b1656f84fc7972d272beb724ab7
Source dataset
uspto-grants-2012_06
Patent number
US08207340B2

Reaction notes

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