Hydrochloric Acid → HCID 25098431, compound

HRID 1095688Notes

Reaction equation

HRID 1095688 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[C:18]([O:25][CH2:26][C@H:27]5[CH2:31][CH2:30][CH2:29][N:28]5C(OC(C)(C)C)=O)[CH:19]=[CH:20][CH:21]=4)[N:16]=3)=[CH:13][N:14]=[C:8]2[CH:7]=1.Cl.O1CCOCC1>C(Cl)(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[C:18]([O:25][CH2:26][C@H:27]5[CH2:31][CH2:30][CH2:29][NH:28]5)[CH:19]=[CH:20][CH:21]=4)[N:16]=3)=[CH:13][N:14]=[C:8]2[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66781917HCID 66781917, compound

Product 1

HCID 25098431HCID 25098431, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

(R)-tert-butyl 2-((2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)methyl)pyrrolidine-1-carboxylate (241 mg, 0.47 mmol) was dissolved in 10 mL of chloroform, followed by addition of 4.0M HCl in dioxane (4.65 ml, 9.3 mmol). The reaction was allowed to stir for 30 hours at ambient temperature at which time all starting material was consumed by LC/TLC. The reaction was concentrated in vacuo, followed by flash column chromatography (eluting with a 1-20% MeOH/DCM gradient), affording an oil on concentration. The crude oil was treated with 1000 uL of 4.0 M HCl in dioxane, affording the desired product (80 mg, 41% yield). MS APCI (+) m/z 419.1 (M+1) detected.

Workup

  1. customwas consumed by LC/TLC
  2. concentrationThe reaction was concentrated in vacuo
  3. washeluting with a 1-20% MeOH/DCM gradient),
  4. customaffording an oil
  5. concentrationon concentration
  6. additionThe crude oil was treated with 1000 uL of 4.0 M HCl in dioxane

Sources & evidence

ORD record
ord-1a90e3e213694eca8128974371aeb492
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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