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

HRID 1678253노트

반응식

HRID 1678253 반응식
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

참가 물질

5

반응물 4

HCID 80711,2-Dimethoxyethane2회HCID 8471TriethylamineHCID 111482324-Chloro-2-(methylsulfonyl)pyrimidineHCID 59023728HCID 59023728, 화합물

생성물 1

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

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-23163a45bd6d45db9f73cbd2a7f6da38
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008481B2

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