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

HRID 916791

반응식

HRID 916791 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([N:26]2[C:30]3[N:31]=[CH:32][N:33]=[C:34]([NH2:35])[C:29]=3[C:28]([C:36](=[O:44])[C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([NH2:43])[CH:38]=3)=[CH:27]2)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]>N1C=CC=CC=1>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([N:26]2[C:30]3[N:31]=[CH:32][N:33]=[C:34]([NH2:35])[C:29]=3[C:28]([C:36](=[O:44])[C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([NH:43][S:9]([C:4]4[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=4)(=[O:11])=[O:10])[CH:38]=3)=[CH:27]2)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

참가 물질

4

반응물 2

HCID 5223883,5-Dichlorobenzenesulfonyl chlorideHCID 672197434-[4-Amino-5-(3-amino-benzoyl)-pyrrolo[2,3-d]pyrimidin-7-yl]-piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 672193824-{4-Amino-5-[3-(3,5-dichloro-benzenesulfonylamino)-benzoyl]-pyrrolo[2,3-d]pyrimidin-7-yl}-piperidine-1-carboxylic acid tert-butyl ester수율 41%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

3,5-Dichlorophenyl sulfonylchloride (2.8 g, 11.5 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 (2.5 g, 5.7 mmol) in pyridine (55 mL). The reaction mixture was stirred at 40 C for 12 h in a sealed tube, quenched with H2O (45 mL), and extracted with EtOAc (3×50 mL). The combined organic extracts were washed with CuSO4 (3×150 mL), H2O (200 mL), and brine (200 mL) and dried (MgSO4), filtered, and concentrated in vacuo. The crude reaction mixture was filtered to obtain the titled compound as an off-white solid (1.5 g, 41%). MS: 646.5 (MH+); HPLC Rf: 6.95 min. (HPLC method 4); HPLC purity: 100%.

후처리

  1. customquenched with H2O (45 mL)
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe combined organic extracts were washed with CuSO4 (3×150 mL), H2O (200 mL), and brine (200 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude reaction mixture
  8. filtrationwas filtered

출처 및 근거

ORD 기록
ord-bbc8861be8454ac0a9df1dde1b1a3dbc
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07271262B2

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