Triethylamine → HCID 178505581, compound

HRID 1272773Notes

Reaction equation

Cl.C(O[C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)=[NH:6])C.C(N(CC)CC)C.[Cl:30][C:31]1[CH:40]=[CH:39][C:34]([C:35]([NH:37][NH2:38])=O)=[CH:33][CH:32]=1>C(O)C>[Cl:30][C:31]1[CH:40]=[CH:39][C:34]([C:35]2[NH:6][C:5]([C:7]3[CH:8]=[C:9]4[C:13](=[CH:14][CH:15]=3)[NH:12][N:11]=[C:10]4[C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)=[N:38][N:37]=2)=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a sealed tube containing ethoxy[3-(4-fluorophenyl)(1H-indazol-5-yl)]methanimine hydrochloride (300 mg, 0.94 mmol) dissolved in ethanol (15 mL) and triethylamine (0.3 μL, 2.82 mmol) was added 4-chlorobenzoic hydrazide (213 mg, 1.25 mmol). The tube was sealed and allowed to stir at 75° C. overnight. The solvent was removed and the material was purified by HPLC to yield the title compound (46 mg, 19% yield). 1H NMR (DMSO-d6) δ 13.5 (s, 1H), 8.75 (s, 1H), 8.0–8.2 (m, 5H), 7.76 (d, 1H), 7.6 (m, 2H), 7.4–7.42 (t, 2H), ES-MS (m/z) 390 [M+1]+.

Workup

customThe tube was sealed
customThe solvent was removed
customthe material was purified by HPLC

Sources & evidence

ORD record: ord-14400c614aec4718857f33e27da1fc2b
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208513B2

Reaction notes

Loading…