3-(Trifluoromethyl)aniline → HCID 11852874, compound

HRID 1660933Notes

Reaction equation

HRID 1660933 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

DIEA (0.15 mL, 0.87 mmol, 4.0 equiv) is added dropwise to a cold (0° C.) mixture of crude (4-imidazo[4,5-c]pyridin-1-yl-phenyl)-acetic acid (55 mg, 0.22 mmol), 3-aminobenzotrifluoride (39 mg, 0.24 mmol, 1.1 equiv), and TBTU (77 mg, 0.24 mmol, 1.1 equiv) in DMF (0.5 mL). The reaction mixture is allowed to warm to rt, stirred for 2 h, diluted with EtOAc and washed with a saturated aqueous solution of NaHCO3, H2O, and brine. The organic phase is dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel column chromatography (CH2Cl2/MeOH, 94:6) to afford the title compound as a white 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. washwashed with a saturated aqueous solution of NaHCO3, H2O, and brine
  2. dry with materialThe organic phase is dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by silica gel column chromatography (CH2Cl2/MeOH, 94:6)

Sources & evidence

ORD record
ord-e4038abceb8b430b9d813ae755f1d7b1
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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