Hydrochloric Acid → HCID 178505550, compound

HRID 1091617Notes

Reaction equation

HRID 1091617 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9](COCC[Si](C)(C)C)[C:10]([C:19]3[CH:20]=[C:21]4[CH:27]=[CH:26][NH:25][C:22]4=[N:23][CH:24]=3)=[C:11]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[N:12]=2)=[CH:4][CH:3]=1.C1C(=O)N([Cl:43])C(=O)C1.Cl>C(#N)C>[Cl:43][C:27]1[C:21]2[C:22](=[N:23][CH:24]=[C:19]([C:10]3[NH:9][C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)=[N:12][C:11]=3[C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[CH:20]=2)[NH:25][CH:26]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31398ChlorosuccinimideHCID 66590952HCID 66590952, compound

Product 1

HCID 178505550HCID 178505550, compoundYield 44.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-(2-(4-fluorophenyl)-4-(pyridin-4-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-5-yl)-1H-pyrrolo[2,3-b]pyridine (18 mg, 0.04 mmol) in ACN (0.6 mL) was added NCS (5 mg, 0.04 mmol). After stirring for 18 h, the reaction mixture was partitioned between EtOAc (20 mL) and aqueous saturated NaHCO3 (10 mL). The layers were separated and the organic phase was washed with aqueous 0.1 M HCl solution (10 mL), brine (10 mL), and dried (Na2SO4). After concentrating in vacuo, the resulting crude product was dissolved in ethanol (1.5 mL) and conc. HCl (0.25 mL, 3 mmol) was added and the reaction was heated at 60° C. for 20 min and then concentrated in vacuo. The crude material was dissolved in DMSO (1.3 mL) and purified by reverse phase HPLC, which after lypholization, yielded 7 mg (38%) of the title compound as the TFA salt: —LC/MS (m/z): 390.1 (MH+), tR=0.67 min.

Workup

  1. customthe reaction mixture was partitioned between EtOAc (20 mL) and aqueous saturated NaHCO3 (10 mL)
  2. customThe layers were separated
  3. washthe organic phase was washed with aqueous 0.1 M HCl solution (10 mL), brine (10 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationAfter concentrating in vacuo
  6. dissolutionthe resulting crude product was dissolved in ethanol (1.5 mL)
  7. concentrationconcentrated in vacuo
  8. dissolutionThe crude material was dissolved in DMSO (1.3 mL)
  9. custompurified by reverse phase HPLC, which after lypholization

Sources & evidence

ORD record
ord-d408afb417594ae7ae2c40c0dc6823b1
Source dataset
uspto-grants-2012_03
Patent number
US08129394B2

Reaction notes

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