2-(4-Hydroxyphenyl)acetohydrazide → 4-(6-Thiazol-2-yl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-phenol

HRID 1921617Notes

Reaction equation

Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[S:9][CH:10]=[CH:11][N:12]=2)=[CH:6][CH:7]=1.[OH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([NH:23][NH2:24])=O)=[CH:16][CH:15]=1>C(O)CCC>[S:9]1[CH:10]=[CH:11][N:12]=[C:8]1[C:5]1[CH:6]=[CH:7][C:2]2[N:3]([C:21]([CH2:20][C:17]3[CH:18]=[CH:19][C:14]([OH:13])=[CH:15][CH:16]=3)=[N:23][N:24]=2)[N:4]=1

Participants

Conditions

Temperature: 120 °C

Procedure

3-Chloro-6-thiazol-2-yl-pyridazine (20 mg, 0.10 mmol) and (4-Hydroxy-phenyl)-acetic acid hydrazide (20 mg, 0.12 mmol) were combined in butanol (5 mL), fitted with water filled condenser and heated to 120° C. overnight. The reaction was concentrated in vacuo followed by purification by HPLC (10-80% CH3CN over 25 min) resulting in the title compound (11.5 mg, 37%) as a white solid. 1H-NMR (CD3OD/CDCl3): δ 8.26-8.24 (1H, d, J=9.6 Hz), 8.17-8.15 (1H, d, J=9.6 Hz), 8.05-8.04 (1H, d, J=3.2 Hz), 7.82-7.81 (1H, d, J=3.0 Hz), 7.32-7.30 (2H, t, J=8.6 Hz), 6.77-6.74 (2H, d, J=8.3 Hz), 4.53 (2H, s). ESI-MS (m/z): Calcd. For C15H11N5OS: 309.07; found: 310.2 (M+H).

Workup

customfitted with water filled condenser
concentrationThe reaction was concentrated in vacuo
customfollowed by purification by HPLC (10-80% CH3CN over 25 min)

Sources & evidence

ORD record: ord-ed03e3992a374504a32b820e56703500
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173654B2

Reaction notes

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