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

반응식

HRID 916786 반응식
[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]

참가 물질

4

반응물 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

생성물 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 ester수율 63%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-0008e36deaed49f18fab3b4e4f016bbf
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07271262B2

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