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

HRID 1094502
Notes
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Reaction equation

HRID 1094502 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-27c74d1021f94711b2235b10c82d6106
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08133886B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes