Hydrochloric Acid → HCID 67517444, compound

HRID 919628Notes

Reaction equation

HRID 919628 reaction equation
[CH3:1][N:2]([C:17]1[C:18]2[CH:25]=[CH:24][N:23]([S:26]([C:29]3[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=3)(=[O:28])=[O:27])[C:19]=2[N:20]=[CH:21][N:22]=1)[CH:3]1[CH2:9][O:8][CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4]1.Cl.C(=O)([O-])[O-]>CO.O1CCOCC1.C(Cl)Cl>[CH3:1][N:2]([C:17]1[C:18]2[CH:25]=[CH:24][N:23]([S:26]([C:29]3[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=3)(=[O:28])=[O:27])[C:19]=2[N:20]=[CH:21][N:22]=1)[CH:3]1[CH2:9][O:8][CH2:7][CH2:6][NH:5][CH2:4]1

Participants

7

Reactant 3

HCID 313Hydrochloric Acid2×HCID 19660Carbonate IonHCID 67517898HCID 67517898, compound

Product 1

HCID 67517444HCID 67517444, compoundYield 110.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of tert-butyl 6-(methyl-(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)-1,4-oxazepane-4-carboxylate (0.142 g, 0.283 mmole) 107.4 in MeOH (5 mL) was treated with 4 M HCl in 1,4-Dioxane (0.28 mL (1.13 mmol) and stirred at rt for 24 hr. An additional of 4 M HCl in 1,4-dioxane (0.4 mL) was added and the mixture stirred for an additional 24 hr and then heated at 50° C. for 2 hours. The mixture was cooled to rt and concentrated in vacuo to give a residue was dissolved in DCM (10 mL) and 5 mL MeOH and neutralized by addition of 0.43 g of polymer-supported carbonate resin (3.5 mmol/g) and stirring at room temperature for 2 hours. The resin was removed by filtered through celite, and the filtrate was concentrated to dryness to yield 125.6 mg of N-methyl-N-(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,4-oxazepan-6-amine 107.5 as a yellowish solid glass that was used without further purification. LCMS (ESI) m/z: 402.20 [M+H]+.

Workup

  1. stirringthe mixture stirred for an additional 24 hr
  2. temperatureheated at 50° C. for 2 hours
  3. temperatureThe mixture was cooled to rt
  4. concentrationconcentrated in vacuo
  5. customto give a residue
  6. stirringstirring at room temperature for 2 hours
  7. customThe resin was removed
  8. filtrationby filtered through celite
  9. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-eb403a55909549848a7e4649ae8f1b07
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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