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Triethylamine → 1-Naphthalenecarboxamide, 6-[(2-amino-4-pyrimidinyl)oxy]-N-[4-fluoro-3-(trifluoromethyl)phenyl]-

HRID 1094502
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HRID 1094502 반응식
[NH2:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15]([C:19](O)=[O:20])=[CH:14][CH:13]=[CH:12]3)[CH:5]=[CH:4][N:3]=1.CCN(CC)CC.[F:29][C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][C:31]=1[C:37]([F:40])([F:39])[F:38].CCCP(=O)=O>CN(C=O)C.CN(C1C=CN=CC=1)C>[F:29][C:30]1[CH:36]=[CH:35][C:33]([NH:34][C:19]([C:15]2[C:16]3[C:11](=[CH:10][C:9]([O:8][C:6]4[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[N:7]=4)=[CH:18][CH:17]=3)[CH:12]=[CH:13][CH:14]=2)=[O:20])=[CH:32][C:31]=1[C:37]([F:38])([F:39])[F:40]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 753774-Fluoro-3-(trifluoromethyl)anilineHCID 16167369Propylphosphoric anhydrideHCID 574551596-(2-Amino-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid

생성물 1

HCID 160715501-Naphthalenecarboxamide, 6-[(2-amino-4-pyrimidinyl)oxy]-N-[4-fluoro-3-(trifluoromethyl)phenyl]-

시약·촉매·용매 2

HCID 14284
4-(Dimethylamino)pyridine
촉매
HCID 6228Dimethylformamide용매

실험 절차

To a suspension of 2.58 g (9.2 mMol) 6-(2-amino-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid in 50 ml DMF, 12.8 ml (92 mMol) Et3N, 490 mg (4.0 mMol) DMAP, 1.41 ml (11 mMol) 4-fluoro-3-trifluoromethyl-aniline and finally 11 ml propylphosphonic anhydride (50% in DMF; 19 mMol) are added. The mixture is stirred for 1 h and then concentrated in vacuo. The residue is diluted with water and EtOAc, the aq. phase is separated off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Column chromatography (SiO2; CH2Cl2/EtOAc 2:1→1:1→1:2) and re-crystallization from CH3CN gives the title compound: m.p.: 205° C.

후처리

  1. additionare added
  2. concentrationconcentrated in vacuo
  3. additionThe residue is diluted with water and EtOAc
  4. customthe aq. phase is separated off
  5. extractionextracted twice with EtOAc
  6. washThe organic layers are washed with water and brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customColumn chromatography (SiO2; CH2Cl2/EtOAc 2:1→1:1→1:2) and re-crystallization from CH3CN

출처 및 근거

ORD 기록
ord-27c74d1021f94711b2235b10c82d6106
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08133886B2

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