HCID 135681577, compound → HCID 135681640, compound

HRID 1354648Notes

Reaction equation

HRID 1354648 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:31])[CH2:9][NH:10][C:11]2[CH:16]=[CH:15][NH:14][C:13](=[O:17])[C:12]=2[C:18]2[NH:19][C:20]3[CH:26]=[C:25]([C:27]([NH2:29])=O)[CH:24]=[C:23]([CH3:30])[C:21]=3[N:22]=2)[CH:5]=[CH:6][CH:7]=1>C1COCC1>[NH2:29][CH2:27][C:25]1[CH:24]=[C:23]([CH3:30])[C:21]2[N:22]=[C:18]([C:12]3[C:13](=[O:17])[NH:14][CH:15]=[CH:16][C:11]=3[NH:10][CH2:9][CH:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[OH:31])[NH:19][C:20]=2[CH:26]=1

Participants

3

Reactant 1

HCID 135681577HCID 135681577, compound

Product 1

HCID 135681640HCID 135681640, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (±)-2-{4-[2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-7-methyl-3H-benzimidazole-5-carboxylic acid amide (20 mg, 0.046 mmol) in THF (1 mL) was added borane-tetrahydrofuran complex (1 M solution) (0.45 mL, 0.45 mmol). The reaction mixture was stirred at room temperature for 10 h and quenched with acetic acid (2 drops). After removal of most solvent, the residue was extracted with EtOAc, washed with brine, dried over Na2SO4. After concentration, the crude product was purified by prep. HPLC to yield the title compound (11.5 mg, 60%). 1H NMR (400 MHz, CD3OD) δ 7.53 (1H, s), 7.50 (1H, s), 7.39 (1H, d, J=7.5 Hz), 7.24–7.32 (3H, m), 7.13 (1H, s), 6.26 (1H, d, J=7.5 Hz), 4.99 (1H, dd, J=4.8, 6.8 Hz), 4.19 (2H, s), 3.72 (1H, dd, J=4.8, 13.6 Hz), 3.64 (1H, dd, J=6.8, 13.6 Hz), 2.62 (3H, s). LCMS (M+H)+ m/z 424 (t=2.10 min.).

Workup

  1. customquenched with acetic acid (2 drops)
  2. customAfter removal of most solvent
  3. extractionthe residue was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentration
  7. customthe crude product was purified by prep

Sources & evidence

ORD record
ord-0d0a5a5fb8354933a6c3a95b822257da
Source dataset
uspto-grants-2007_05
Patent number
US07223757B2

Reaction notes

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