Hydrochloric Acid → HCID 178482137, compound

HRID 1623413Notes

Reaction equation

HRID 1623413 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH2:22][C@H]4CCCN(C(OC(C)(C)C)=O)C4)[N:16]=3)[C:12]([Cl:36])=[CH:11][N:10]=2)[CH2:4][CH2:3]1.[C:37](=[O:54])(ON1C(=O)CCC1=O)[O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.Cl.O1[CH2:61][CH2:60]OCC1>C(OCC)(=O)C.C(Cl)Cl>[Cl:36][C:12]1[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N:21]([C@H:61]3[CH2:60][CH2:4][CH2:5][NH:8][CH2:9]3)[CH3:22])[N:16]=2)=[CH:14][C:9]([NH:8][C@H:5]2[CH2:6][CH2:7][C@H:2]([NH:1][C:37](=[O:54])[O:38][CH2:39][C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH2:3][CH2:4]2)=[N:10][CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 83172Benzyl succinimido carbonateHCID 178451957HCID 178451957, compound

Product 1

HCID 178482137HCID 178482137, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (R)-tert-butyl 3-((2′-(trans-4-aminocyclohexylamino)-5′-chloro-2,4′-bipyridin-6-yl-amino)methyl)piperidine-1-carboxylate (36 mg, 0.070 mmol), DCM (1.2 ml), TEA (0.019 ml, 0.140 mmol) and benzyl 2,5-dioxopyrrolidin-1-yl carbonate (26.1 mg, 0.105 mmol) was stirred at ambient temperature for 2 hours and the reaction progress was followed by LCMS. To this crude reaction mixture was added 25 ml of ethyl acetate, washed with 2M sodium carbonate, water (2×) and saturated salt solution (1×), dried with sodium sulfate, filtered, concentrated to crude intermediate. To the crude intermediate was added 4M HCl in Dioxane (2 ml, 8.00 mmol) and stirred at ambient temperature for 1 hour. The crude reaction mixture was concentrated to constant mass, dissolved in 1 ml of DMSO and purified by prep LC. After lypohilization, 15 mg of the title compound, was obtained as a TFA salt. LCMS (m/z): 549.4 (MH+), retention time=0.67 min.

Workup

  1. customTo this crude reaction mixture
  2. washwashed with 2M sodium carbonate, water (2×) and saturated salt solution (1×)
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to crude intermediate
  6. stirringstirred at ambient temperature for 1 hour
  7. customThe crude reaction mixture
  8. concentrationwas concentrated to constant mass
  9. dissolutiondissolved in 1 ml of DMSO
  10. custompurified by prep LC

Sources & evidence

ORD record
ord-9b025b9606614f9c9aaac4a8cd3f9855
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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