Potassium Hydroxide → HCID 86720284, compound

HRID 1777487Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[O:23][CH:22]=[N:21][CH:20]=3)=[CH:15][CH:14]=2)=[S:11])[CH:4]=1)[CH3:2].[Br-].[Br-].[Br-].C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.[OH-].[K+]>C(O)(=O)C.O>[CH2:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[S:11][C:18]3[CH:17]=[C:16]([C:19]4[O:23][CH:22]=[N:21][CH:20]=4)[CH:15]=[CH:14][C:13]=3[N:12]=2)[CH:4]=1)[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

1-(4-Ethylpyridin-2-yl)-3-(4-(oxazol-5-yl)phenyl)thiourea (0.27 g, 0.8 mmol) was dissolved in 5 mL of acetic acid. Benzyltrimethylammonium tribromide (320 mg, 0.821 mmol) was then added directly. The mixture was stirred at 50° C. for 1 hour. The mixture was cooled to 0° C. and diluted with 15 mL of water. The resulting solution was then made basic through addition of solid KOH pellets. The resulting precipitate was collected by vacuum filtration, washed with water and dried under vacuum to afford the crude product as a tan solid. A portion of the solid was purified by rp-HPLC affording 0.6 mg of N-(4-ethylpyridin-2-yl)-6-(oxazol-5-yl)benzo[d]thiazol-2-amine 501 as a yellow solid. MS calculated for C17H14N4OS: 323.0888; [M+H]+. found: 322.93. 1H-NMR (400 MHz, MeOD) 8.25-8.23 (m, 2H), 8.17 (s, 1H), 7.75 (d, J=8.4, 1H), 7.66 (d, J=8.4, 1H) 7.50 (s, 1H), 6.97 (s, 1H), 6.88 (d, J=8.4, 1H), 2.68 (q, J=7.7, 2H), 1.28 (t, J=7.7, 3H).

Workup

temperatureThe mixture was cooled to 0° C.
filtrationThe resulting precipitate was collected by vacuum filtration
washwashed with water
customdried under vacuum
customto afford the crude product as a tan solid
customA portion of the solid was purified by rp-HPLC

Sources & evidence

ORD record: ord-8acbc259b51f4d47b2a218ae29ef4c37
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266874B2

Reaction notes

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