Hydrochloric Acid → 5-(6-methoxy-1H-benzimidazol-2-yl)-6'-piperazin-1-yl-[3,3']bipyridinyl-6-ylamine

HRID 241411Notes

Reaction equation

HRID 241411 reaction equation
Cl.[NH2:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][C:12]([N:15]3[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]3)=[CH:13][CH:14]=2)=[CH:5][C:4]=1[C:28]1[NH:32][C:31]2[CH:33]=[C:34]([O:37][CH3:38])[CH:35]=[CH:36][C:30]=2[N:29]=1>O1CCOCC1>[CH3:38][O:37][C:34]1[CH:35]=[CH:36][C:30]2[N:29]=[C:28]([C:4]3[CH:5]=[C:6]([C:9]4[CH:10]=[N:11][C:12]([N:15]5[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]5)=[CH:13][CH:14]=4)[CH:7]=[N:8][C:3]=3[NH2:2])[NH:32][C:31]=2[CH:33]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67494746tert-butyl 4-[6'-amino-5'-(6-methoxy-1 H-benzimidazol-2-yl)-[3,3']bipyridinyl-6-yl]piperazine-1-carboxylate

Product 1

HCID 509246255-(6-methoxy-1H-benzimidazol-2-yl)-6'-piperazin-1-yl-[3,3']bipyridinyl-6-ylamine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3 ml of 4M HCl in dioxane are added to tert-butyl 4-[6′-amino-5′-(6-methoxy-1 H-benzimidazol-2-yl)-[3,3′]bipyridinyl-6-yl]piperazine-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 purified by means of RP-HPLC and lyophilised, giving 5-(6-methoxy-1H-benzimidazol-2-yl)-6′-piperazin-1-yl-[3,3′]bipyridinyl-6-ylamine as free base; HPLC-MS [M+H]+ 402.2.

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
  7. customThe residue is purified by means of RP-HPLC

Sources & evidence

ORD record
ord-3c75a797949c4df0b0b9c31fe420f940
Source dataset
uspto-grants-2014_02
Patent number
US08648201B2

Reaction notes

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