反応式
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[N:8][NH:9]2)=[C:5]([C:12]2[N:16]3[N:17]=[C:18]([C:21](O)=[O:22])[CH:19]=[CH:20][C:15]3=[N:14][CH:13]=2)[CH:4]=1.F[B-](F)(F)F.[N:31]1([O:40][C:41](N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[Cl-].[NH4+].CCN(CC)CC.CN(C=[O:61])C>>[C:41]([OH:40])([C:2]([F:25])([F:24])[F:1])=[O:61].[F:25][C:2]([F:24])([F:1])[C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[N:8][NH:9]2)=[C:5]([C:12]2[N:16]3[N:17]=[C:18]([C:21]([NH2:31])=[O:22])[CH:19]=[CH:20][C:15]3=[N:14][CH:13]=2)[CH:4]=1参加物
反応物 5
生成物 2
実験手順
To 3-(6-(trifluoromethyl)-1H-indazol-4-yl)imidazo[1,2-b]pyridazine-6-carboxylic acid (0.036 g, 0.104 mmol) in DMF (3 mL) was added O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.028 g, 0.073 mmol), ammonium chloride (8.32 mg, 0.156 mmol), and Et3N (0.013 g, 0.124 mmol). The reaction mixture was stirred at room temperature overnight and was subsequently filtered and purified by preparative HPLC, eluting with a gradient of 25-50% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) to give a TFA salt of the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.35-7.46 (m, 1H), 7.53 (t, J=7.58 Hz, 1H), 7.71 (d, J=8.59 Hz, 1H), 7.82 (dd, J=18.32, 9.47 Hz, 1H), 7.95-8.05 (m, 2H), 8.40 (t, J=9.35 Hz, 1H), 8.50 (br s, 1H), 8.57-8.66 (m, 1H), 8.70 (s, 1H); ESI-MS m/z [M+H]+ calc'd for C15H9F3N6O, 347.1. found 347.2.
後処理
- filtrationwas subsequently filtered
- custompurified by preparative HPLC
- washeluting with a gradient of 25-50% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA)
出典と根拠
- ORDレコード
- ord-2b74a432e6084df582e038350dce3192
- 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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