HCID 46205769, compound → 2-[4-(4-Piperidinyl)phenyl]-1H-benzimidazole-7-carboxamide

HRID 2366448Notes

Reaction equation

HRID 2366448 reaction equation
[NH2:1][C:2]1[C:7]([C:8](=[O:10])[NH2:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]2)=[CH:16][CH:15]=1)=O>C(O)(=O)C>[NH:23]1[CH2:24][CH2:25][CH:20]([C:17]2[CH:16]=[CH:15][C:14]([C:12]3[NH:11][C:3]4[CH:4]=[CH:5][CH:6]=[C:7]([C:8]([NH2:9])=[O:10])[C:2]=4[N:1]=3)=[CH:19][CH:18]=2)[CH2:21][CH2:22]1

Participants

3

Reactant 1

HCID 46205769HCID 46205769, compound

Product 1

HCID 166653912-[4-(4-Piperidinyl)phenyl]-1H-benzimidazole-7-carboxamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of EXAMPLE 1A (0.175 g) in acetic acid (2 mL) at reflux was stirred for 90 minutes and concentrated. The concentrate was dissolved in water, treated with 50% aqueous NaOH (0.2 mL) and filtered. The filtrate was concentrated and purified by high performance liquid chromatography (HPLC) on a C18 column with 0-100% CH3CN/water/0.1% trifluoroacetic acid (TFA). 1H NMR (DMSO-d6) δ 9.25 (s, 1H), 8.61 (s, 1H), 8.34 (s, 1H), 8.22 (d, J=8.42 Hz, 1H), 7.87 (d, J=6.55 Hz, 1H), 7.74 (d, J=7.18 Hz, 2H), 7.46 (d, J=8.11 Hz, 2H), 7.35 (t, J=7.80 Hz, 1H), 3.42 (d, J=12.48 Hz, 2H), 3.01-3.09 (m, 2H), 2.97 (ddd, J=12.01, 8.58, 3.43 Hz, 1H), 2.00 (s, 2H), 1.84 (qd, J=13.05, 3.90 Hz, 2H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe concentrate was dissolved in water
  3. additiontreated with 50% aqueous NaOH (0.2 mL)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by high performance liquid chromatography (HPLC) on a C18 column with 0-100% CH3CN/water/0.1% trifluoroacetic acid (TFA)

Sources & evidence

ORD record
ord-2ef4e2b5b2fc40a8836d69b862b2d512
Source dataset
uspto-grants-2014_04
Patent number
US08697736B2

Reaction notes

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