3,5-Dichlorophenyl isocyanate → 4-(4-Amino-5-{3-[3-(3,5-dichloro-phenyl)-ureido]-benzoyl}-pyrrolo[2,3-d]pyrimidin-7-yl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 916786

反応式

HRID 916786 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([N:25]2[C:29]3[N:30]=[CH:31][N:32]=[C:33]([NH2:34])[C:28]=3[C:27]([C:35](=[O:43])[C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([NH2:42])[CH:37]=3)=[CH:26]2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]>N1C=CC=CC=1>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([N:25]2[C:29]3[N:30]=[CH:31][N:32]=[C:33]([NH2:34])[C:28]=3[C:27]([C:35](=[O:43])[C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([NH:42][C:10]([NH:9][C:4]4[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=4)=[O:11])[CH:37]=3)=[CH:26]2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

参加物

4

反応物 2

HCID 944603,5-Dichlorophenyl isocyanateHCID 672197434-[4-Amino-5-(3-amino-benzoyl)-pyrrolo[2,3-d]pyrimidin-7-yl]-piperidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 672191604-(4-Amino-5-{3-[3-(3,5-dichloro-phenyl)-ureido]-benzoyl}-pyrrolo[2,3-d]pyrimidin-7-yl)-piperidine-1-carboxylic acid tert-butyl ester収率 63%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

3,5-Dichlorophenyl isocyanate (0.26 g, 1.37 mmol) was added to a solution of 4-[4-amino-5-(3-amino-benzoyl)-pyrrolo[2,3-d]pyrimidin-7-yl]-piperidine-1-carboxylic acid tert-butyl ester (0.5 g, 1.15 mmol) in pyridine (13 mL). The reaction mixture was stirred at 75 C for 4.5 h and room temperature for 12 h in a sealed tube, quenched with H2O (13 mL), and extracted with EtOAc (4×15 mL). The combined organic extracts were washed with CuSO4 (3×15 mL), H2O (20 mL), and brine (30 mL) and dried (MgSO4), filtered, and concentrated in vacuo. The crude reaction mixture was triturated in CH2Cl2 and filtered to obtain the titled compound as a white solid (0.45 g, 63%). MS: 625.5 (MH+); HPLC Rf: 7.48 min. (HPLC method 4); HPLC purity: 100%.

後処理

  1. customquenched with H2O (13 mL)
  2. extractionextracted with EtOAc (4×15 mL)
  3. washThe combined organic extracts were washed with CuSO4 (3×15 mL), H2O (20 mL), and brine (30 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude reaction mixture
  8. customwas triturated in CH2Cl2
  9. filtrationfiltered

出典と根拠

ORDレコード
ord-0008e36deaed49f18fab3b4e4f016bbf
出典データセット
uspto-grants-2007_09
特許番号
US07271262B2

関連ノート

読み込み中…