Triethylamine → 1-[4-(3-Amino-1H-pyrazolo[3,4-b]pyridin-6-yl)phenyl]-3-(2-fluoro-5-trifluoromethylphenyl)urea

HRID 556438ノート

反応式

HRID 556438 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]3[NH:14][N:15]=[C:16]([NH2:17])[C:11]3=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][C:27]=1[N:36]=[C:37]=[O:38]>C1COCC1>[NH2:17][C:16]1[C:11]2[C:12](=[N:13][C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:37]([NH:36][C:27]4[CH:28]=[C:29]([C:32]([F:33])([F:35])[F:34])[CH:30]=[CH:31][C:26]=4[F:25])=[O:38])=[CH:7][CH:6]=3)=[CH:9][CH:10]=2)[NH:14][N:15]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 27333802-Fluoro-5-(trifluoromethyl)phenyl isocyanateHCID 178507390HCID 178507390、化合物

生成物 1

HCID 1785092201-[4-(3-Amino-1H-pyrazolo[3,4-b]pyridin-6-yl)phenyl]-3-(2-fluoro-5-trifluoromethylphenyl)urea

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

100 mg (0.44 mmol) of 6-(4-aminophenyl)-1H-pyrazolo[3,4-b]pyridin-3-ylamine are partially solubilized in 2.5 ml of anhydrous THF. The mixture is then degassed for 15 minutes with argon. 61.55 μl (44.93 mg, 0.44 mmol, 1 eq.) of triethylamine are subsequently added. The solution is once again degassed for 15 minutes. Finally, 64.22 μl (91 mg, 0.44 mmol, 1 eq.) of 2-fluoro-5-(trifluoromethyl)phenyl isocyanate are added dropwise. The mixture is stirred for 2 hours at ambient temperature under an inert atmosphere. After reaction, the mixture is filtered. The filtrate is concentrated. A beige solid is isolated. This crude product is subsequently purified on a C18 reverse-phase silica (13 g) column with an eluent gradient of 5% to 95% of acetonitrile in water. The fractions containing the expected product are lyophilized. A white solid is isolated (10 mg).

後処理

  1. customThe mixture is then degassed for 15 minutes with argon
  2. customThe solution is once again degassed for 15 minutes
  3. customAfter reaction
  4. filtrationthe mixture is filtered
  5. concentrationThe filtrate is concentrated
  6. customA beige solid is isolated
  7. customThis crude product is subsequently purified on a C18 reverse-phase silica (13 g) column with an eluent gradient of 5% to 95% of acetonitrile in water
  8. additionThe fractions containing the expected product
  9. customA white solid is isolated (10 mg)

出典と根拠

ORDレコード
ord-d127445927234e37b4723b709a20434e
出典データセット
uspto-grants-2011_11
特許番号
US08058290B2

反応ノート

読み込み中…