Triethylamine → HCID 23653200, compound

HRID 1094512Notes

Reaction equation

HRID 1094512 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([O:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[C:23](O)=[O:24])[CH:14]=2)[CH:9]=[CH:8][N:7]=1)=[O:5])[CH3:2].CCN(CC)CC.[NH2:33][C:34]1[CH:35]=[CH:36][C:37]([F:44])=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:39]=1.CCCP(=O)=O>CN(C=O)C.CN(C1C=CN=CC=1)C.O.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([O:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[C:23](=[O:24])[NH:33][C:34]3[CH:35]=[CH:36][C:37]([F:44])=[C:38]([C:40]([F:43])([F:41])[F:42])[CH:39]=3)[CH:14]=2)[CH:9]=[CH:8][N:7]=1)=[O:5])[CH3:2]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 753774-Fluoro-3-(trifluoromethyl)anilineHCID 16167369Propylphosphoric anhydrideHCID 59175974HCID 59175974, compound

Product 1

HCID 23653200HCID 23653200, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 242 mg (0.717 mMol) 4-(5-carboxy-naphthalen-2-yloxy)-pyrimidine-2-carboxylic acid ethyl ester in 10.7 ml DMF, 1.5 ml (10.8 mMol) Et3N, 38 mg (0.31 mMol) DMAP, 111 μl (0.86 mMol) 5-amino-2-fluorobenzotrifluoride and 880 μl propylphosphonic anhydride (50% in DMF; 1.5 mMol) are added. After 30 min stirring, the reaction mixture is diluted with water and EtOAc, the aq. phase separated off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; CH2Cl2→CH2Cl2/acetone 19:1) gives the title compound: MS: [M+1]+=500; TLC (CH2Cl2/acetone 9:1): Rf=0.54.

Workup

  1. customthe aq. phase separated off
  2. extractionextracted twice with EtOAc
  3. washThe organic layers are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-698ef674008c43baada5e025792ad124
Source dataset
uspto-grants-2012_03
Patent number
US08133886B2

Reaction notes

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