4-Methylmorpholine → 4-(4-{5-[2-Chloro-5-(4-Cyano-Benzoylamino)-Benzoylamino]-Pyrimidin-2-ylamino}-Benzenesulfonyl)-Piperidine-1-Carboxylic Acid tert-Butyl Ester

HRID 1662825노트

반응식

HRID 1662825 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:21])[C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1.[C:40]([O:44][C:45]([N:47]1[CH2:52][CH2:51][CH:50]([S:53]([C:56]2[CH:61]=[CH:60][C:59]([NH:62][C:63]3[N:68]=[CH:67][C:66]([NH2:69])=[CH:65][N:64]=3)=[CH:58][CH:57]=2)(=[O:55])=[O:54])[CH2:49][CH2:48]1)=[O:46])([CH3:43])([CH3:42])[CH3:41]>C(Cl)Cl>[C:40]([O:44][C:45]([N:47]1[CH2:48][CH2:49][CH:50]([S:53]([C:56]2[CH:57]=[CH:58][C:59]([NH:62][C:63]3[N:68]=[CH:67][C:66]([NH:69][C:4](=[O:6])[C:3]4[CH:7]=[C:8]([NH:11][C:12](=[O:21])[C:13]5[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=5)[CH:9]=[CH:10][C:2]=4[Cl:1])=[CH:65][N:64]=3)=[CH:60][CH:61]=2)(=[O:54])=[O:55])[CH2:51][CH2:52]1)=[O:46])([CH3:43])([CH3:41])[CH3:42]

참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 587487264-(4-(5-Amino-pyrimidin-2-ylamino)-benzenesulfonyl)-piperidine-1-carboxylic acid tert-butyl esterHCID 607484272-Chloro-5-(4-Cyano-Benzoylamino)-Benzoic Acid

생성물 1

HCID 674282094-(4-{5-[2-Chloro-5-(4-Cyano-Benzoylamino)-Benzoylamino]-Pyrimidin-2-ylamino}-Benzenesulfonyl)-Piperidine-1-Carboxylic Acid tert-Butyl Ester수율 38.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Intermediate 16 (Example 24) (0.132 g, 0.439 mmol) was combined with 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) (0.093 g, 0.53 mmol) and diluted with DCM (4 mL). This was immediately treated with 4-methyl morpholine (0.10 mL, 0.88 mmol) and allowed to stir at ambient temperature for 1 h. Intermediate 13 (Example 20) (0.20 g, 0.462 mmol) was then added in one portion. Stirring was continued overnight. After 18 h, reaction solvents were removed and resulting crude solids purified via HPLC to afford the title compound as a white solid (0.12 g, 36%).

후처리

  1. stirringStirring
  2. waitwas continued overnight
  3. waitAfter 18 h
  4. customreaction solvents
  5. customwere removed
  6. customresulting crude solids
  7. custompurified via HPLC

출처 및 근거

ORD 기록
ord-baaa9eb1b0304648ad15980e3850fcf8
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030487B2

반응 노트

불러오는 중…