HCID 67346507, compound → N-(3-fluoro-4-(2-(4-oxocyclohex-1-enyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide

HRID 1676373Notes

Reaction equation

HRID 1676373 reaction equation
O1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[S:19][C:18]4[C:13](=[N:14][CH:15]=[CH:16][C:17]=4[O:20][C:21]4[CH:26]=[CH:25][C:24]([NH:27][C:28]([C:30]5[C:31](=[O:43])[N:32]([C:36]6[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=6)[N:33]=[CH:34][CH:35]=5)=[O:29])=[CH:23][C:22]=4[F:44])[CH:12]=3)=[CH:7][CH2:6]2)[O:4]CC1>C(O)(C(F)(F)F)=O>[F:44][C:22]1[CH:23]=[C:24]([NH:27][C:28]([C:30]2[C:31](=[O:43])[N:32]([C:36]3[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=3)[N:33]=[CH:34][CH:35]=2)=[O:29])[CH:25]=[CH:26][C:21]=1[O:20][C:17]1[CH:16]=[CH:15][N:14]=[C:13]2[CH:12]=[C:11]([C:8]3[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH:7]=3)[S:19][C:18]=12

Participants

3

Reactant 1

HCID 67346507HCID 67346507, compound

Product 1

HCID 58949478N-(3-fluoro-4-(2-(4-oxocyclohex-1-enyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamideYield 28.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A round-bottomed flask was charged with N-(4-(2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide (153 mg, 0.249-mmol) and CF3COOH (10 mL). The reaction mixture was stirred at room temperature until the starting material had been consumed (overnight). Then the solvent was removed and the residue was purified by silica gel chromatography (dichloromethane/7 M NH3 in MeOH from 50/1 to 10/1, v/v) to give product (40.8 mg, 28.7%). LRMS (APCI pos): >99% purity, 254 nm, m/e 571 (M+1). 1H NMR (400 MHz, CDCl3) δ 11.84 (s, 1H), 8.45 (d, 1H), 8.41 (d, 1H), 8.24 (d, 1H), 7.96 (d, 1H), 7.58-7.62 (m, 2H), 7.40 (m, 1H), 7.20-7.28 (m, 4H), 6.51 (d, 1H), 6.42 (m, 1H), 3.14 (m, 2H), 3.02 (m, 2H), 2.71 (m, 2H).

Workup

  1. customhad been consumed (overnight)
  2. customThen the solvent was removed
  3. customthe residue was purified by silica gel chromatography (dichloromethane/7 M NH3 in MeOH from 50/1 to 10/1

Sources & evidence

ORD record
ord-15a59ef1424d4693b106837adf88d60c
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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