Hydrochloric Acid → HCID 57594674, compound

HRID 1714556Notes

Reaction equation

HRID 1714556 reaction equation
[Br:1][C:2]1[C:3]2[N:4]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][C@H:18]([NH:31][C:32](=[O:38])OC(C)(C)C)[CH2:19][N:20]4[C:28](=[O:29])[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[C:21]4=[O:30])=[CH:13][CH:12]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1.Cl.C(N(C(C)C)CC)(C)C.[Cl:49][C:50]1[CH:51]=[C:52]([CH:67]=[CH:68][C:69]=1[O:70][CH:71]([CH3:73])[CH3:72])C(OC1C(F)=C(F)C(F)=C(F)C=1F)=O>O1CCOCC1.C(OCC)(=O)C>[Br:1][C:2]1[C:3]2[N:4]([CH:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([CH2:17][C@H:18]([NH:31][C:32](=[O:38])[C:52]4[CH:67]=[CH:68][C:69]([O:70][CH:71]([CH3:72])[CH3:73])=[C:50]([Cl:49])[CH:51]=4)[CH2:19][N:20]4[C:28](=[O:29])[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[C:21]4=[O:30])=[CH:15][CH:16]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 57594128HCID 57594128, compoundHCID 57594575HCID 57594575, compound

Product 1

HCID 57594674HCID 57594674, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1,1-dimethylethyl {(1S)-2-[4-(8-bromoimidazo[1,2-a]pyridin-2-yl)phenyl]-1-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]ethyl}carbamate (3.5 mmol) and hydrogen chloride in 1,4-dioxane (20 mL, 4.0M) stirred for 1 h at RT. The reaction was concentrated to dryness and redissolved in N,N-dimethylformamide (35 mL). Added to the solution was diisopropylethylamine (10.5 mmol) and pentafluorophenyl 3-chloro-4-[(1-methylethyl)oxy]benzoate (3.8 mmol), which was stirred at RT for half an hour. The reaction was dissolved in ethyl acetate (80 mL) and washed with water (3×50 mL) and brine (1×50 mL). To the separated organic layer was added hexanes (150 mL) upon which a precipitate was formed, filtered, and dried to afford the title compound as an off white solid (65%). ESMS [M+H]+: 672.2.

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. dissolutionredissolved in N,N-dimethylformamide (35 mL)
  3. additionAdded to the solution
  4. washwashed with water (3×50 mL) and brine (1×50 mL)
  5. additionTo the separated organic layer was added hexanes (150 mL) upon which a precipitate
  6. customwas formed
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-4965ed47039d4a77b52198f8da283cbe
Source dataset
uspto-grants-2010_09
Patent number
US07795448B2

Reaction notes

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