Trifluoroacetic acid → N-(3-Fluoro-4-(2-(4-oxocyclohexyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide

HRID 1676376ノート

反応式

HRID 1676376 の反応式
O1[C:5]2([CH2:10][CH2:9][CH: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)[CH2:7][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]([CH:8]3[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]3)[S:19][C:18]=12

参加物

3

反応物 2

HCID 6422Trifluoroacetic acidHCID 67347914N-(4-(2-(1,4-dioxaspiro[4.5]decan-8-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide

生成物 1

HCID 58949495N-(3-Fluoro-4-(2-(4-oxocyclohexyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide収率 42.9%

実験手順

A round-bottomed flask was charged with N-(4-(2-(1,4-dioxaspiro[4.5]decan-8-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide (13.3 mg, 0.0216 mmol) and CF3COOH (5 mL). The reaction mixture was stirred at room temperature the starting material had been consumed (1 hour). Then the solvent was removed and the residue was purified by silica gel chromatography (DCM/7 M NH3 in MeOH from 50/1 to 10/1, v/v) to give product (5.3 mg, 42.9%). LRMS (APCI pos): >99% purity, 254 nm, m/e 573 (M+1). 1H NMR (400 MHz, CD3OD) δ 11.84 (s, 1H), 8.46 (d, 1H), 8.41 (d, 1H), 8.24 (d, 1H), 7.95 (dd, 1H), 7.57-7.65 (m, 2H), 7.39 (m, 1H), 7.34 (s, 1H), 7.21-7.30 (m, 3H), 6.49 (d, 1H), 3.45 (m, 1H), 2.34-2.61 (m, 6H), 2.09 (m, 2H).

後処理

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

出典と根拠

ORDレコード
ord-6bddb25c74f748829fc947ed7056efaa
出典データセット
uspto-grants-2011_08
特許番号
US08003662B2

反応ノート

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