1,4-Dioxane → HCID 69014357, compound

HRID 542062Notes

Reaction equation

HRID 542062 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[NH:6][C:7]3[CH:8]=[N:9][CH:10]=[C:11]([CH:32]=3)[CH2:12][CH2:13][C:14]3[CH:22]=[C:18]([NH:19][C:20]=1[N:21]=2)[CH:17]=[CH:16][C:15]=3[O:23][CH2:24][C:25]([O:27]C(C)(C)C)=[O:26].O1CCOCC1>Cl>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[NH:6][C:7]3[CH:8]=[N:9][CH:10]=[C:11]([CH:32]=3)[CH2:12][CH2:13][C:14]3[CH:22]=[C:18]([NH:19][C:20]=1[N:21]=2)[CH:17]=[CH:16][C:15]=3[O:23][CH2:24][C:25]([OH:27])=[O:26]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 57962043HCID 57962043, compound

Product 1

HCID 69014357HCID 69014357, compoundYield 307.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of tert-butyl {[6-chloro-2,4,8,18,22-pentaazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaen-12-yl]oxy}acetate (0.76 g, 1.7 mmol) in 4 M HCl in 1,4 dioxane (30 mL, 120 mmol) was heated at 70° C. for 1 h. The reaction mixture was concentrated to a solid that was suspended in diethyl ether, filtered, and washed with diethyl ether to give the desired product (0.82 g, 104%) as a white solid. LCMS for C19H17ClN5O3 (M+H)+: m/z=398.0.

Workup

  1. concentrationThe reaction mixture was concentrated to a solid
  2. filtrationfiltered
  3. washwashed with diethyl ether

Sources & evidence

ORD record
ord-2b4056182bbe49a8be5d5e68f3f6d871
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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