1,2-Dimethoxyethane → 4-(7-Benzo[b]thiophen-2-yl-1H-indazol-5-ylamino)-pyrimidin-2-ol

HRID 1678253ノート

反応式

HRID 1678253 の反応式
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4](S(C)(=O)=O)[N:3]=1.[S:12]1[C:16]([C:17]2[CH:18]=[C:19]([NH2:26])[CH:20]=[C:21]3[C:25]=2[NH:24][N:23]=[CH:22]3)=[CH:15][C:14]2[CH:27]=[CH:28][CH:29]=[CH:30][C:13]1=2.C(N(CC)CC)C.C[O:39]CCOC>>[S:12]1[C:16]([C:17]2[CH:18]=[C:19]([NH:26][C:2]3[CH:7]=[CH:6][N:5]=[C:4]([OH:39])[N:3]=3)[CH:20]=[C:21]3[C:25]=2[NH:24][N:23]=[CH:22]3)=[CH:15][C:14]2[CH:27]=[CH:28][CH:29]=[CH:30][C:13]1=2

参加物

5

反応物 4

HCID 80711,2-Dimethoxyethane2 回HCID 8471TriethylamineHCID 111482324-Chloro-2-(methylsulfonyl)pyrimidineHCID 59023728HCID 59023728、化合物

生成物 1

HCID 1785177614-(7-Benzo[b]thiophen-2-yl-1H-indazol-5-ylamino)-pyrimidin-2-ol収率 0.1%

実験手順

To a mixture of 4-chloro-2-methanesulfonyl-pyrimidine (Preparation #1, 1.35 g, 7.0 mmol) in DME (10 mL) was added a mixture of 7-benzo[b]thiophen-2-yl-1H-indazol-5-ylamine (Example #F.8.1, 1.03 g, 3.9 mmol) and triethylamine (0.76 mL, 5.4 mmol) in DME (70 mL). After about 16 hours at ambient temperature the mixture was filtered, and the solid was purified by reverse phase preparative HPLC (Thermo Hypersil-Keystone 250×21.2 mm 8μ Hypersil® HS C18 column; 5% CH3CN/50 mM aqueous ammonium acetate hold for 5 min; 5-50% CH3CN/50 mM aqueous ammonium acetate over 20 min; 50-100% CH3CN/50 mM aqueous ammonium acetate over 1 min; hold at 100% CH3CN for 5 minutes, 21 mL/min) to yield 4-(7-Benzo[b]thiophen-2-yl-1H-indazol-5-ylamino)-pyrimidin-2-ol (2 mg, 0.006 mmol, 0.1% yield): LC/MS Rt (Method e) 1.3 min; m/z (M−H)− 358.3.

後処理

  1. additionwas added
  2. filtrationAfter about 16 hours at ambient temperature the mixture was filtered
  3. customthe solid was purified by reverse phase preparative HPLC (Thermo Hypersil-Keystone 250×21.2 mm 8μ Hypersil® HS C18 column; 5% CH3CN/50 mM aqueous ammonium acetate hold for 5 min; 5-50% CH3CN/50 mM aqueous ammonium acetate over 20 min; 50-100% CH3CN/50 mM aqueous ammonium acetate over 1 min; hold at 100% CH3CN for 5 minutes, 21 mL/min)

出典と根拠

ORDレコード
ord-23163a45bd6d45db9f73cbd2a7f6da38
出典データセット
uspto-grants-2011_08
特許番号
US08008481B2

反応ノート

読み込み中…