3,5-Bis(trifluoromethyl)benzoic acid → HCID 60196489, compound

HRID 878178Notes

Reaction equation

HRID 878178 reaction equation
[C:1]1([CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[NH:13][CH2:14][C:15]#[N:16].[F:18][C:19]([F:34])([F:33])[C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[C:23](O)=[O:24]>>[C:15]([CH2:14][N:13]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:7]=1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH3:17])[C:23](=[O:24])[C:22]1[CH:26]=[C:27]([C:29]([F:30])([F:31])[F:32])[CH:28]=[C:20]([C:19]([F:18])([F:33])[F:34])[CH:21]=1)#[N:16]

Participants

3

Reactant 2

HCID 128893,5-Bis(trifluoromethyl)benzoic acidHCID 86670773HCID 86670773, compound

Product 1

HCID 60196489HCID 60196489, compound

Procedure

The title compound was prepared in analogy to example 90, from (4-o-tolyl-pyridin-3-ylamino)-acetonitrile and 3,5-bis-trifluoromethyl-benzoic acid (CAS RN 725-89-3) after a reaction time of 18 hours. The compound was purified by silica gel chromatography on a 20 g column using a MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). The product-containing fractions were pooled and evaporated until a suspension formed. The colorless solid was filtered off and washed with a small amount of a mixture of EtOAc:n-heptane (1:6). Colorless solid (37%). MS (ESI): m/z=464.12 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography on a 20 g column
  2. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)
  3. customevaporated until a suspension
  4. customformed
  5. filtrationThe colorless solid was filtered off
  6. washwashed with a small amount of a mixture of EtOAc:n-heptane (1:6)

Sources & evidence

ORD record
ord-abacb446956f4da98483afa97b625259
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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