Sodium Hydroxide → 2-(3-(6-cyclopropylpyrazin-2-yl)-1H-indol-5-yl)-5-phenyl-1,3,4-thiadiazole

HRID 634241Notes

Reaction equation

[CH:1]1([C:4]2[N:9]=[C:8]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([C:19]5[S:20][C:21]([C:24]6[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=6)=[N:22][N:23]=5)[CH:17]=4)[N:12](S(C4C=CC(C)=CC=4)(=O)=O)[CH:11]=3)[CH:7]=[N:6][CH:5]=2)[CH2:3][CH2:2]1.O1CCOCC1.[OH-].[Na+]>O>[CH:1]1([C:4]2[N:9]=[C:8]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([C:19]5[S:20][C:21]([C:24]6[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=6)=[N:22][N:23]=5)[CH:17]=4)[NH:12][CH:11]=3)[CH:7]=[N:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 100 °C

Procedure

In a 20 mL glass microwave tube 2-(3-(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-5-phenyl-1,3,4-thiadiazole (190 mg, 0.346 mmol) was treated with dioxane (2.5 mL) and 1N NaOH (0.75 mL) and heated in the microwave to 100° C. for 10 min. The mixture was treated with H2O, extracted with EtOAc (2×15 mL), washed with brine, dried over MgSO4, filtered and concentrated affording 2-(3-(6-cyclopropylpyrazin-2-yl)-1H-indol-5-yl)-5-phenyl-1,3,4-thiadiazole (89 mg, 65%) as a yellow amorphous solid. (ESI, pos. ion) m/z: 396.0 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.06 (1H, br. s.), 9.13 (1H, s), 8.96 (1H, s), 8.43 (1H, d, J=2.5 Hz), 8.40 (1H, s), 7.99-8.08 (2H, m), 7.89-7.96 (1H, m), 7.58-7.69 (4H, m), 2.23-2.32 (1H, m), 1.17-1.30 (4H, m).

Workup

extractionextracted with EtOAc (2×15 mL)
washwashed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-89da5a596d2b4bef86fb1679a7011ccd
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321756B2

Reaction notes

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