Trifluoroacetic acid → 3-(2-(1-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-5-methylpyrimidin-4-yl)benzoic acid

HRID 2401956Notes

Reaction equation

HRID 2401956 reaction equation
[F:1][C:2]1([F:37])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:14]([NH:16][C:17]4[N:22]=[C:21]([C:23]5[CH:24]=[C:25]([CH:33]=[CH:34][CH:35]=5)[C:26]([O:28]C(C)(C)C)=[O:27])[C:20]([CH3:36])=[CH:19][N:18]=4)=[O:15])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1.C(O)(C(F)(F)F)=O>>[F:37][C:2]1([F:1])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:14]([NH:16][C:17]4[N:22]=[C:21]([C:23]5[CH:24]=[C:25]([CH:33]=[CH:34][CH:35]=5)[C:26]([OH:28])=[O:27])[C:20]([CH3:36])=[CH:19][N:18]=4)=[O:15])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57856175Tert-butyl 3-(2-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-5-methylpyrimidin-4-yl)benzoate

Product 1

HCID 578561393-(2-(1-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-5-methylpyrimidin-4-yl)benzoic acid

Procedure

To tert-butyl 3-(2-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-5-methylpyrimidin-4-yl)benzoate (48 mg, 0.094 mmol) dichloromethane (1 mL) and TFA (726 μL) were added and stirred at room temperature for four hours. The dichloromethane and TFA were evaporated under reduced pressure. The crude product was dissolved in DMSO (1 mL), filtered and purified by reverse phase preparative HPLC to yield 3-(2-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-5-methylpyrimidin-4-yl)benzoic acid. ESI-MS m/z calc. 453.11, found 454.3 (M+1)+. Retention time 1.63 minutes.

Workup

  1. customThe dichloromethane and TFA were evaporated under reduced pressure
  2. dissolutionThe crude product was dissolved in DMSO (1 mL)
  3. filtrationfiltered
  4. custompurified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-ee8121f1c114478696f070c767fe0387
Source dataset
uspto-grants-2014_08
Patent number
US08796312B2

Reaction notes

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