Sodium Hydroxide → 5-(3-(4-(isopropylamino)pyrimidin-2-yl)-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine

HRID 634104Notes

Reaction equation

[CH:1]([NH:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]4[O:24][C:23]([NH2:25])=[N:22][N:21]=4)[CH:18]=3)[N:13](S(C3C=CC(C)=CC=3)(=O)=O)[CH:12]=2)[N:6]=1)([CH3:3])[CH3:2].[OH-].[Na+]>O1CCOCC1>[CH:1]([NH:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]4[O:24][C:23]([NH2:25])=[N:22][N:21]=4)[CH:18]=3)[NH:13][CH:12]=2)[N:6]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 5-(3-(4-(isopropylamino)pyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (400 mg, 0.817 mmol) in p-dioxane (4 mL) was added aq. 10% NaOH (2 mL). The mixture was heated at 100° C. for 2 h. The reaction was quenched with ice cold H2O and the resulting precipitate was filtered, washed with ice cold H2O and dried. The residue was purified with RP-HPLC to 5-(3-(4-(isopropylamino)pyrimidin-2-yl)-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (60 mg, 22%) as an off-yellow solid. MS (ESI, pos. ion) m/z: 335.9 (M+1); 1H-NMR (400 MHz, DMSO-d6): δ 11.77 (d, J=2 Hz, 1H), 9.02 (s, 1H), 8.14-8.07 (m, 2H), 7.65 (dd, J=2, 8.8 Hz, 1H), 7.55 (d, J=8 Hz, 1H), 7.11-7.06 (m, 3H), 6.24 (d, J=8 Hz, 1H), 4.33 (brs, 1H), 1.26 (d, J=6.8 Hz, 6H).

Workup

customThe reaction was quenched with ice cold H2O
filtrationthe resulting precipitate was filtered
washwashed with ice cold H2O
customdried
customThe residue was purified with RP-HPLC to 5-(3-(4-(isopropylamino)pyrimidin-2-yl)-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (60 mg, 22%) as an off-yellow solid

Sources & evidence

ORD record: ord-50c3f07079a94e16a5c13f98fc77275b
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321756B2

Reaction notes

Loading…