Hydrochloric Acid → HCID 50923465, compound

HRID 241409Notes

Reaction equation

HRID 241409 reaction equation
Cl.[NH2:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][N:12]([CH:14]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)[CH:13]=2)=[CH:5][C:4]=1[C:27]1[NH:31][C:30]2[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=2[N:28]=1>O1CCOCC1>[NH:31]1[C:30]2[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=2[N:28]=[C:27]1[C:4]1[C:3]([NH2:2])=[N:8][CH:7]=[C:6]([C:9]2[CH:10]=[N:11][N:12]([CH:14]3[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]3)[CH:13]=2)[CH:5]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67495021HCID 67495021, compound

Product 1

HCID 50923465HCID 50923465, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5 ml of 4M HCl in dioxane are added to 41.8 mg (0.091 mmol) of tert-butyl 4-{4-[6-amino-5-(1H-benzimidazol-2-yl)pyridin-3-yl]pyrazol-1-yl}piperidine-1-carboxylate, and the mixture is stirred at room temperature for 14 h. The reaction mixture is evaporated to dryness, and water is added. The aqueous phase is adjusted to pH>10 using 2N NaOH and extracted 3× with ethyl acetate. The organic phases are dried using sodium sulfate, filtered and evaporated. The residue is lyophilised, giving 3-(1H-benzimidazol-2-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)pyridin-2-ylamine as free base; HPLC-MS [M+H]+ 360.2;

Workup

  1. customThe reaction mixture is evaporated to dryness, and water
  2. additionis added
  3. extractionextracted 3× with ethyl acetate
  4. customThe organic phases are dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-b5fb187bfa4944b3a402c4f783c71f52
Source dataset
uspto-grants-2014_02
Patent number
US08648201B2

Reaction notes

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