Hydrochloric Acid → HCID 57594674, compound

HRID 1785040Notes

Reaction equation

HRID 1785040 reaction equation
CC([N:5]([C@H:9]([CH2:27][N:28]1[C:36](=[O:37])[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]1=[O:38])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:18]=[C:19]3[C:24]([Br:25])=[CH:23][CH:22]=[CH:21][N:20]3[CH:26]=2)=[CH:13][CH:12]=1)[C:6](=O)[O-:7])(C)C.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:25][C:24]1[C:19]2[N:20]([CH:26]=[C:17]([C:14]3[CH:13]=[CH:12][C:11]([CH2:10][C@H:9]([NH:5][C:6](=[O:7])[C:52]4[CH:67]=[CH:68][C:69]([O:70][CH:71]([CH3:72])[CH3:73])=[C:50]([Cl:49])[CH:51]=4)[CH2:27][N:28]4[C:29](=[O:38])[C:30]5[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=5)[C:36]4=[O:37])=[CH:16][CH:15]=3)[N:18]=2)[CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 57594128HCID 57594128, compoundHCID 86608900HCID 86608900, 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-2yl)methyl]ethyl)carbamate (3.5 mmol) and hydrogen chloride in 1,4-dioxane (20 mL, 4.0 M) was 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), followed by stirring 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-e45590cc49e643b99b114b7b14e81c1d
Source dataset
uspto-grants-2009_03
Patent number
US07504413B2

Reaction notes

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