Acetic Acid → HCID 10138816, compound

HRID 456924Notes

Reaction equation

HRID 456924 reaction equation
O=[CH:2][CH2:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]1[C:14](=[O:23])[NH:15][C:16]3[C:21]([CH:22]=1)=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:7]2.[CH3:24][S:25]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)(=[O:27])=[O:26].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:24][S:25]([N:28]1[CH2:33][CH2:32][N:31]([CH2:2][CH2:3][C:4]2[CH:5]=[C:6]3[C:10](=[CH:11][CH:12]=2)[NH:9][C:8]([C:13]2[C:14](=[O:23])[NH:15][C:16]4[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:7]3)[CH2:30][CH2:29]1)(=[O:27])=[O:26]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7091611-(Methylsulfonyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 18436972HCID 18436972, compound

Product 1

HCID 10138816HCID 10138816, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A slurry of the 3-{5-[2-oxoethyl]-1H-indol-2-yl}quinolin-2(1H)-one (10-2, 75 mg, 0.25 mmol, 1 equiv) and 1-(methylsulfonyl)piperazine (163 mg, 1.0 mmol, 4 equiv) in 1,2-dichloroethane(100 mL) was treated with acetic acid (0.67 mg, 1.12 mmol, 4.5 equiv) and sodium triacetoxyborohydride (156 mg, 0.75 mmol, 3 equiv) and the reaction was stirred under ambient conditions for 18 hours. The reaction was concentrated and the residue was partitioned between EtOAc and sat. NaHCO3 solution. The organic layer was washed with brine, dried over magnesium sulfate and concentrated. The residue was purified by chromatography on a silica column. Elution with EtOAc to 5% NH3-EtOH/EtOAc gave 3-(5-{2-[4-(methyl-sulfonyl)piperazin-1-yl]ethyl}-1H-indol-2-yl)quinolin-2(1H)-one (10-3) as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 12.2 (s, 1H), 11.4 (s, 1H), 8.52 (s, 1H), 7.72 (d, J=8 Hz, 1H), 7.51 (t, J=8 Hz, 1 H), 7.42 (d, J=8 Hz, 1 H), 7.38 (m, 2 H), 7.25 (m, 2H), 6.99 (d, J=8 Hz, 1H), 3.11 (m, 4 H), 3.87 (s, 3H), 2.81 (br t, J=8 Hz, 2 H), 2.61 (br t, J=8 Hz, 2H), 2.56 (m, 4 H).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was partitioned between EtOAc and sat. NaHCO3 solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on a silica column
  7. washElution with EtOAc to 5% NH3-EtOH/EtOAc

Sources & evidence

ORD record
ord-4471dc8690884161b4bb7f0e41243d44
Source dataset
uspto-grants-2007_03
Patent number
US07186723B2

Reaction notes

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