反応式
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[N:8][NH:9]2)=[C:5]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([C:18]([OH:20])=O)[CH:13]=2)[CH:4]=1.[Cl-].[NH4+].C1C=CC2N([OH:34])N=[N:31]C=2C=1.C(Cl)CCl.C(N(C(C)C)C(C)C)C.CN([CH:51]=[O:52])C>>[C:51]([OH:52])([C:2]([F:22])([F:21])[F:1])=[O:34].[F:21][C:2]([F:1])([F:22])[C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[N:8][NH:9]2)=[C:5]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([C:18]([NH2:31])=[O:20])[CH:13]=2)[CH:4]=1参加物
反応物 6
生成物 2
実験手順
To a mixture of 4-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinic acid (0.028 g, 0.091 mmol) in DMF (3 mL) were added ammonium chloride (0.024 g, 0.456 mmol), HOBt (0.018 g, 0.137 mmol), and EDC (0.028 g, 0.146 mmol), followed by N-ethyl-N-isopropylpropan-2-amine (0.079 mL, 0.456 mmol). The reaction mixture was stirred for 18 hours at room temperature. The crude reaction mixture was subsequently purified by preparative HPLC, eluting with a gradient of 30-35% acetonitrile (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 6.5 minutes. The product-containing fractions were combined and the solvent removed in vacuo to give a TFA salt of the title compound as an off white solid (0.012 g, 43%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.68 (s, 1H), 7.80 (br s, 1H), 7.95-8.15 (m, 2H), 8.27 (br s, 1H), 8.32-8.47 (m, 2H), 8.81 (d, J=5.05 Hz, 1H), 13.89 (br s, 1H); ESI-MS m/z [M+H]+ calc'd for C14H9F3N4O, 307.1. found 307.11.
後処理
- customThe crude reaction mixture
- customwas subsequently purified by preparative HPLC
- washeluting with a gradient of 30-35% acetonitrile (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 6.5 minutes
- customthe solvent removed in vacuo
出典と根拠
- ORDレコード
- ord-768d7102f4d84836a4deb09f4e519dc5
- 出典データセット
- uspto-grants-2016_09
- 特許番号
- US09434743B2
関連ノート
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