Sodium Hydroxide → HCID 68328330, compound

HRID 634289Notes

Reaction equation

HRID 634289 reaction equation
[CH:1]([O:4][C:5]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]4[N:24]=[C:23]([NH:25][C:26](=[O:28])[CH3:27])[O:22][N:21]=4)[CH:18]=3)[N:13](S(C3C=CC(C)=CC=3)(=O)=O)[CH:12]=2)[CH:8]=[N:7][CH:6]=1)([CH3:3])[CH3:2].[OH-].[Na+]>O1CCOCC1>[CH:1]([O:4][C:5]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]4[N:24]=[C:23]([NH:25][C:26](=[O:28])[CH3:27])[O:22][N:21]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[N:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68328366HCID 68328366, compound

Product 1

HCID 68328330HCID 68328330, compoundYield 5.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-(3-(3-(6-isopropoxypyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,2,4-oxadiazol-5-yl)acetamide (220 mg, 0.47 mmol) in 1,4-dioxane (2.0 mL) was added 10% aq NaOH (1.0 mL) and the reaction was stirred at RT for 48 h. The mixture was treated with ice cold water (5.0 mL) and the precipitate was filtered and washed with water. The crude product was purified with preparative HPLC (eluent: 50-80% MeCN in water with 0.01% TFA) to give N-(3-(3-(6-isopropoxypyrazin-2-yl)-1H-indol-5-yl)-1,2,4-oxadiazol-5-yl)acetamide (10 mg, 5.6%). MS (ESI, pos. ion) m/z: 379.2 (M+1); 1H NMR (400 MHz, DMSO-d6): δ 12.10 (brs, 2H), 9.17 (s, 1H), 8.74 (s, 1H), 8.42 (d, J=2.4 Hz, 1H), 7.96 (s, 1H), 7.82 (dd, J=8.4, 1.2 Hz, 1H), 7.62 (d, J=8.4 Hz, 1H), 5.53-5.47 (m, 1H), 2.23 (s, 3H), 1.51 (d, J=6.4 Hz, 6H).

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with water
  3. customThe crude product was purified with preparative HPLC (eluent: 50-80% MeCN in water with 0.01% TFA)

Sources & evidence

ORD record
ord-b3afcc74a5a94f6688ee9250bcc8679d
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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