Oxalyl chloride → N-(5-tert-butyl-2-methoxy-3-(methylsulfonamido)phenyl)-2-(4-(2-morpholinopyrimidin-4-yloxy)naphthalen-1-yl)-2-oxoacetamide

HRID 2075568노트

반응식

HRID 2075568 반응식
[N:1]1([C:7]2[N:12]=[C:11]([O:13][C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]([C:24](=[O:28])[C:25]([OH:27])=O)=[CH:16][CH:15]=3)[CH:10]=[CH:9][N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.[NH2:35][C:36]1[C:37]([O:51][CH3:52])=[C:38]([NH:46][S:47]([CH3:50])(=[O:49])=[O:48])[CH:39]=[C:40]([C:42]([CH3:45])([CH3:44])[CH3:43])[CH:41]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[C:42]([C:40]1[CH:39]=[C:38]([NH:46][S:47]([CH3:50])(=[O:49])=[O:48])[C:37]([O:51][CH3:52])=[C:36]([NH:35][C:25](=[O:27])[C:24]([C:17]2[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:14]([O:13][C:11]3[CH:10]=[CH:9][N:8]=[C:7]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)[N:12]=3)=[CH:15][CH:16]=2)=[O:28])[CH:41]=1)([CH3:45])([CH3:43])[CH3:44]

참가 물질

7

반응물 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 10214710N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamideHCID 59379818[4-(2-Morpholin-4-yl-pyrimidin-4-yl-oxy)-naphthalen-1-yl]-oxo-acetic acid

생성물 1

HCID 16734161N-(5-tert-butyl-2-methoxy-3-(methylsulfonamido)phenyl)-2-(4-(2-morpholinopyrimidin-4-yloxy)naphthalen-1-yl)-2-oxoacetamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

[4-(2-Morpholin-4-yl-pyrimidin-4-yl-oxy)-naphthalen-1-yl]-oxo-acetic acid (16) obtained above (36 mg, 0.095 mmol) was dissolved in 2 mL DCM and oxalyl chloride (0.08 mL, 0.949 mmol) was added, followed by catalytic DMF. The reaction mixture was stirred at rt, after which N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide (14) (26 mg, 0.096 mmol) and DIEA (0.05 mL, 0.284 mmol) were added, and stirring was continued for 12 hr. The reaction mixture was concentrated in vacuo and the residue was purified by LC/MS (10-100% AcN/H2O over 8.5 min.) Calculated mass=444. Observed mass=444.

후처리

  1. stirringstirring
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was purified by LC/MS (10-100% AcN/H2O over 8.5 min.)

출처 및 근거

ORD 기록
ord-c8b0cfa6322f42afb7787285ded6768e
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919617B2

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