홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Trifluoroacetic acid → Diethyl (4-{[4-{[2-(methylcarbamoyl)phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate

HRID 511206
노트
인쇄 미리보기

반응식

HRID 511206 반응식
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[NH2:13][C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1[C:16]([NH:18][CH3:19])=[O:17].C(N(C(C)C)CC)(C)C.ClC1N=C(NC2C=CC=CC=2C(NC)=O)C(C(F)(F)F)=CN=1.ClC1C(C(F)(F)F)=CN=C(NC2C=CC=CC=2C(NC)=O)N=1.[NH2:77][C:78]1[CH:92]=[CH:91][C:81]([CH2:82][P:83](=[O:90])([O:87][CH2:88][CH3:89])[O:84][CH2:85][CH3:86])=[CH:80][CH:79]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:19][NH:18][C:16]([C:15]1[CH:20]=[CH:21][CH:22]=[CH:23][C:14]=1[NH:13][C:6]1[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=[C:2]([NH:77][C:78]2[CH:79]=[CH:80][C:81]([CH2:82][P:83](=[O:90])([O:84][CH2:85][CH3:86])[O:87][CH2:88][CH3:89])=[CH:91][CH:92]=2)[N:7]=1)=[O:17]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 7

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 88358Diethyl p-aminobenzylphosphonateHCID 3080722-Amino-N-methylbenzamideHCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidineHCID 866338612-((2-Chloro-5-(trifluoromethyl)pyrimidin-4-yl)amino)-N-methylbenzamide2회
HCID 87326917
2-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-N-methylbenzamide

생성물 1

HCID 49821264Diethyl (4-{[4-{[2-(methylcarbamoyl)phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Reaction of 2,4-dichloro-5-(trifluoromethyl)pyrimidine XL with commercially available 2-amino-N-methyl-benzamide and diisopropylethylamine at room temperature overnight affords a mixture of 2-{[2-chloro-5-(trifluoromethyl)pyrimidin-4-yl]amino}-N-methylbenzamide and 2-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-N-methylbenzamide (XLIIIa/XLIII b). Trituration of the mixture with methylene chloride affords a pure sample of the desired 4-substitiuted product XLIIIa. Concentration of the mother liquors and purification of the residue by chromatography over silica gel using 5% EtOAc in methylene chloride as eluent isolating the less polar material affords further pure 4-substituted isomer plus a mixture of isomers which may be subjected to further chromatography if desired. Reaction of pure 2-{[2-chloro-5-(trifluoromethyl)pyrimidin-4-yl]amino}-N-methylbenzamide XLIIIa with anilines such as diethyl (4-aminobenzyl)phosphonate in the presence of TFA and TFE under microwave irradiation yields the desired products (e.g. diethyl (4-{[4-{[2-(methylcarbamoyl)phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate, Ex. 20)

후처리

  1. customaffords
  2. customConcentration of the mother liquors and purification of the residue by chromatography over silica gel using 5% EtOAc in methylene chloride as eluent
  3. customisolating the less polar material
  4. customaffords further pure 4-substituted isomer
  5. additiona mixture of isomers which
  6. customunder microwave irradiation
  7. customyields the desired products (e.g. diethyl (4-{[4-{[2-(methylcarbamoyl)phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate, Ex. 20)

출처 및 근거

ORD 기록
ord-d254b62abe6f499abd529113894a9f9e
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09096624B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트