HCID 59534641, compound → HCID 59534648, compound

HRID 593680Notes

Reaction equation

HRID 593680 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]=[CH2:12])=[C:3]1[C:13]1[CH:14]=[C:15]([NH:19][S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])[CH:16]=[N:17][CH:18]=1>CO>[CH2:11]([C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:2]([CH3:1])[C:3]=1[C:13]1[CH:14]=[C:15]([NH:19][S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])[CH:16]=[N:17][CH:18]=1)[CH3:12]

Participants

3

Reactant 1

HCID 59534641HCID 59534641, compound

Product 1

HCID 59534648HCID 59534648, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A flask is charged with ethanesulfonic acid [5-(1-methyl-3-vinyl-1H-indol-2-yl)-pyridin-3-yl]-amide (35 mg, 0.082 mmol) and MeOH (5 mL). The flask is evacuated and flushed with N2 thrice. Pd/C (4.36 mg) is added and the reaction stirred under H2 overnight at 50° C. The reaction is filtered over celite and the celite layer is washed thoroughly with MeOH. The filtrate is concentrated in vacuo. The crude is purified by silica gel flash chromatography (dichloromethane-methanol, 19:1) followed by HPLC purification using Xbridge C18 eluting with a 10 to 100% acetonitrile-water gradient to afford the pure product ethanesulfonic acid [5-(3-ethyl-1-methyl-1H-indol-2-yl)-pyridin-3-yl]-amide. 1H NMR (400 MHz, MeOD) δ ppm 1.27 (t, J=7.6 Hz, 3H), 1.40 (t, J=7.3 Hz, 3H), 2.76 (q, J=7.6 Hz, 2H), 3.25 (q, J=7.3 Hz, 2H), 3.66 (s, 3H), 7.09-7.17 (m, 1H), 7.23-7.31 (m, 1H), 7.43 (d, J=8.3 Hz, 1H), 7.65 (d, J=7.8 Hz, 1H), 7.83 (t, J=2.3 Hz, 1H), 8.36 (d, J=1.8 Hz, 1H), 8.49 (d, J=2.5 Hz, 1H). HRMS: (ESI) m/z 344.1435 [(M+H)+ Calcd for C18H21N3O2S 344.1427].

Workup

  1. customThe flask is evacuated
  2. customflushed with N2 thrice
  3. additionPd/C (4.36 mg) is added
  4. filtrationThe reaction is filtered over celite
  5. washthe celite layer is washed thoroughly with MeOH
  6. concentrationThe filtrate is concentrated in vacuo
  7. customThe crude is purified by silica gel flash chromatography (dichloromethane-methanol, 19:1)
  8. customfollowed by HPLC purification
  9. washC18 eluting with a 10 to 100% acetonitrile-water gradient

Sources & evidence

ORD record
ord-31abb3d677e1423ebda570bda3f5f345
Source dataset
uspto-grants-2016_01
Patent number
US09242963B2

Reaction notes

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