Sodium Hydroxide → HCID 68328897, compound

HRID 634317Notes

Reaction equation

HRID 634317 reaction equation
[CH:1]([NH:4][C:5]1[O:9][C:8]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15](S(C2C=CC(C)=CC=2)(=O)=O)[CH:14]=[C:13]3[C:29]2[N:34]=[C:33]([C:35]([NH:37][CH3:38])=[O:36])[CH:32]=[CH:31][CH:30]=2)=[N:7][N:6]=1)([CH3:3])[CH3:2].[OH-].[Na+]>O1CCOCC1>[CH:1]([NH:4][C:5]1[O:9][C:8]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH:14]=[C:13]3[C:29]2[N:34]=[C:33]([C:35]([NH:37][CH3:38])=[O:36])[CH:32]=[CH:31][CH:30]=2)=[N:7][N:6]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68328865HCID 68328865, compound

Product 1

HCID 68328897HCID 68328897, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 6-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1-tosyl-1H-indol-3-yl)-N-methylpicolinamide (100 mg, 0.189 mmol) in 1,4-dioxane (2 mL) was added aq.NaOH (7 M, 2 mL) and the reaction was heated at 90° C. for 1 h. The reaction was then quenched with water to get a precipitate. The precipitate was filtered and washed with water (2×100 mL) and dried. The crude product was crystallized from 20% EtOAc in petroleum ether (3×10 mL) to give 6-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1H-indol-3-yl)-N-methylpicolinamide (16 mg, 23%). MS (ESI, pos. ion) m/z: 377.2 (M+1); 1H NMR (400 MHz, DMSO-d6) δ 12.21 (s, 1H), 8.67-8.69 (m, 2H), 8.48 (s, 1H), 8.00 (d, 2H, J=4.0 Hz), 7.80-7.82 (m, 1H), 7.69 (dd, 1H, J=8.4, 1.6 Hz), 7.63 (d, 1H, J=8.4 Hz), 7.59 (d, 1H, J=7.6 Hz), 3.71-3.78 (m, 1H), 2.93 (d, 3H, J=4.8 Hz), 1.23 (d, 6H, J=6.4 Hz).

Workup

  1. customThe reaction was then quenched with water
  2. customto get a precipitate
  3. filtrationThe precipitate was filtered
  4. washwashed with water (2×100 mL)
  5. customdried
  6. customThe crude product was crystallized from 20% EtOAc in petroleum ether (3×10 mL)

Sources & evidence

ORD record
ord-85c28990ebbe4cf58c5b6b536a92aa2c
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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