Sodium Hydroxide → HCID 68327959, compound

HRID 634320Notes

Reaction equation

HRID 634320 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[CH:30]=[N:31][CH:32]=[C:33]([CH:38]=2)[C:34]([NH:36][CH3:37])=[O:35])=[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[CH:30]=[N:31][CH:32]=[C:33]([CH:38]=2)[C:34]([NH:36][CH3:37])=[O:35])=[N:7][N:6]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68328437HCID 68328437, compound

Product 1

HCID 68327959HCID 68327959, compoundYield 28.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1-tosyl-1H-indol-3-yl)-N-methylnicotinamide (150 mg, 0.283 mmol) in 1,4-dioxane (3 mL) was added aq.NaOH (7 M, 3 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 purified with preparative HPLC (eluting with 30-70% MeCN in water with 0.1% TFA in each solvent) to give 5-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1H-indol-3-yl)-N-methylnicotinamide (30 mg, 28%). MS (ESI, pos. ion) m/z: 377.1 (M+1); 1H NMR (400 MHz, DMSO-d6) δ 11.95 (s, 1H), 9.04 (d, 1H, J=2.0 Hz), 8.89 (d, 1H, J=2.0 Hz), 8.74-8.76 (m, 1H), 8.44-8.45 (m, 1H), 8.24 (s, 1H), 8.02 (d, 1H, J=2.0 Hz), 7.73 (dd, 1H, J=8.8, 2.0 Hz), 7.62-7.66 (m, 2H), 3.71-3.76 (m, 1H), 2.85 (d, 3H, J=4.4 Hz), 1.22 (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 purified with preparative HPLC (
  7. washeluting with 30-70% MeCN in water with 0.1% TFA in each solvent)

Sources & evidence

ORD record
ord-3406824d932144ebbca65b61e50cb237
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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