Hydrochloric Acid → HCID 178511939, compound

HRID 983796Notes

Reaction equation

HRID 983796 reaction equation
Cl.[OH:2][C:3]1[C:8]([C:9]2[NH:10][C:11]3[CH:16]=[CH:15][N:14]=[CH:13][C:12]=3[N:17]=2)=[CH:7][CH:6]=[CH:5][C:4]=1[C:18]1[NH:22][C:21]2[CH:23]=[CH:24][C:25]([C:27]([NH2:29])=[NH:28])=[CH:26][C:20]=2[N:19]=1>CO.O=[Pt]=O>[OH:2][C:3]1[C:8]([C:9]2[NH:17][C:12]3[CH2:13][NH:14][CH2:15][CH2:16][C:11]=3[N:10]=2)=[CH:7][CH:6]=[CH:5][C:4]=1[C:18]1[NH:22][C:21]2[CH:23]=[CH:24][C:25]([C:27]([NH2:29])=[NH:28])=[CH:26][C:20]=2[N:19]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178511938HCID 178511938, compound

Product 1

HCID 178511939HCID 178511939, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

PtO2 (20 mg) and concentrated hydrochloric acid (5 mL) was added to a solution of 2-[2-Hydroxy-3-(1H-imidazo[4,5-c]pyridin-2-yl)-phenyl]-1H-benzoimidazole-5-carboxamidine (Example 120, Table 2) (100 mg, 0.27 mmol) in MeOH (20 mL). The mixture was hydrogenated at 50 psi in a Parr apparatus for 12-18 h. After the hydrogenation was completed, the catalyst was filtered and the filtrate was concentrated to dryness. HPLC purification (2-50% acetonitrile/60 minutes) followed by lyophilization afforded 2-[2-Hydroxy-3-(4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridin-2-yl)-phenyl]-1H-benzoimidazole-5-carboxamidine 75 as pale yellow powder (20 mg, 20% yield) (Example 296, Table 2a).

Workup

  1. filtrationthe catalyst was filtered
  2. concentrationthe filtrate was concentrated to dryness
  3. customHPLC purification (2-50% acetonitrile/60 minutes)

Sources & evidence

ORD record
ord-ea8766a981f04d82a0020e8af0052480
Source dataset
uspto-grants-2005_03
Patent number
US06867200B1

Reaction notes

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