1,4-Dioxane hydrochloride → HCID 59740849, compound

HRID 547369Notes

Reaction equation

HRID 547369 reaction equation
[C:1]1([C:6]2[CH:30]=[CH:29][C:9]([C:10]([NH:12][CH2:13][C:14]3[C:15]([CH2:20][NH:21]C(=O)OC(C)(C)C)=[N:16][CH:17]=[CH:18][CH:19]=3)=[O:11])=[C:8]([NH:31][CH2:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[CH:35]=3)[N:7]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1.Cl.O1CCOCC1>CO>[NH2:21][CH2:20][C:15]1[C:14]([CH2:13][NH:12][C:10](=[O:11])[C:9]2[CH:29]=[CH:30][C:6]([C:1]3[CH2:5][CH2:4][CH2:3][CH:2]=3)=[N:7][C:8]=2[NH:31][CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[CH:35]=2)=[CH:19][CH:18]=[CH:17][N:16]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 59740842HCID 59740842, compound

Product 1

HCID 59740849HCID 59740849, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-butyl (3-((6-cyclopentenyl-2-(3-fluorophenethylamino)nicotinamido)methyl)pyridin-2-yl)methylcarbamate was dissolved in MeOH (1 mL) and allowed to stir at room temperature. HCl/dioxane (4M, 2 mL) was added dropwise and stirred until complete. The reaction mixture was concentrated, diluted with EtOAc, washed with saturated sodium bicarbonate, brine and dried (Na2SO4). The organics were concentrated and purified by RP-HPLC with a mixture of acetonitrile and H2O to give N-((2-(aminomethyl)pyridin-3-yl)methyl)-6-cyclopentenyl-2-(3-fluorophenethylamino)nicotinamide as a solid (0.026 g, 25%). LC/MS (M+H+) m/z 446.2.

Workup

  1. stirringstirred until complete
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with EtOAc
  4. washwashed with saturated sodium bicarbonate, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationThe organics were concentrated
  7. custompurified by RP-HPLC with a mixture of acetonitrile and H2O

Sources & evidence

ORD record
ord-1ff548f8b9634705bf7f9e7ada8cfb3e
Source dataset
uspto-grants-2011_05
Patent number
US07939534B2

Reaction notes

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