3-(Trifluoromethyl)aniline → HCID 11852874, compound

HRID 1010708Notes

Reaction equation

HRID 1010708 reaction equation
CCN(C(C)C)C(C)C.[N:10]1([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][C:26]([OH:28])=O)=[CH:21][CH:20]=2)[C:18]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N:12]=[CH:11]1.[NH2:29][C:30]1[CH:31]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:33]=[CH:34][CH:35]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[N:10]1([C:19]2[CH:20]=[CH:21][C:22]([CH2:25][C:26]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:37])([F:38])[F:39])[CH:31]=3)=[O:28])=[CH:23][CH:24]=2)[C:18]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N:12]=[CH:11]1

Participants

7

Reactant 4

HCID 73753-(Trifluoromethyl)anilineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67021528HCID 67021528, compound

Product 1

HCID 11852874HCID 11852874, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.15 ml of DIEA are added dropwise to a cold (0° C.) mixture of 55 mg of crude (4-imidazo[4,5-c]pyridin-1-yl-phenyl)-acetic acid, 39 mg of 3-aminobenzotrifluoride and 77 mg of TBTU in 0.5 ml of DMF. The mixture obtained is allowed to warm to rt, stirred for 2 hours, diluted with EtOAc and washed with a saturated aqueous solution of NaHCO3, H2O, and brine. The organic phase obtained is dried (Na2SO4), filtered and concentrated in vacuo. The evaporation residue obtained is purified by silica gel column chromatography. 2-(4-Imidazo[4,5-c]pyridin-1-yl-phenyl)-N-(3-trifluoromethyl-phenyl]-acetamide is obtained in the form of a solid: ES-MS: 397.0 [M+H]+; single peak at tR=3.52 min (System 1); Rf=0.18 (CH2Cl2/MeOH, 94:6).

Workup

  1. customThe mixture obtained
  2. washwashed with a saturated aqueous solution of NaHCO3, H2O, and brine
  3. customThe organic phase obtained
  4. dry with materialis dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe evaporation residue obtained
  8. customis purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4e32b7d7a86b4e9c9e94a5f0a66fb498
Source dataset
uspto-grants-2011_07
Patent number
US07977338B2

Reaction notes

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