Trifluoroacetic acid → HCID 66695735, compound

HRID 1808874Notes

Reaction equation

HRID 1808874 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:13]([C:14]([OH:16])=O)=[C:12]([CH3:17])[O:11][N:10]=1.[Cl:18][C:19]1[C:25]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:24][C:22]([NH2:23])=[C:21]([CH:32]=[CH2:33])[CH:20]=1.C(O)(C(F)(F)F)=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>C(Cl)Cl.O.CN1C(=O)CCC1>[NH2:23][C:22]1[C:21]([CH:32]=[CH2:33])=[CH:20][C:19]([Cl:18])=[C:25]([N:26]2[CH2:27][CH2:28][N:29]([C:14]([C:13]3[C:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[O:2][CH3:1])=[N:10][O:11][C:12]=3[CH3:17])=[O:16])[CH2:30][CH2:31]2)[CH:24]=1

Participants

9

Reactant 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 64841003-(2-Methoxyphenyl)-5-methyl-1,2-oxazole-4-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 666922704-Chloro-5-(piperazin-1-yl)-2-vinylaniline

Product 1

HCID 66695735HCID 66695735, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To the mixture of 3-(2-methoxyphenyl)-5-methylisoxazole-4-carboxylic acid (0.182 g, 0.779 mmol), 4-chloro-5-(piperazin-1-yl)-2-vinylaniline, 2 TFA (0.279 g, 0.599 mmol) and HATU (0.296 g, 0.779 mmol) in a 100-mL round bottom flask was added NMP (5.5 mL) and triethylamine (0.145 g, 1.438 mmol). The resulted solution was stirred at room temperature for 13 hours. Water (50 mL) and DCM (50 mL) were added to the reaction mixture and the two phases were separated in a separatory funnel. The aqueous phase was extracted with DCM (2×40 mL). Solvent was evaporated by rotavap. The product was purified by preparative HPLC (acetonitrile/water−10 nM ammonium acetate) to give 0.146 g (54% yield) of the title compound.

Workup

  1. customthe two phases were separated in a separatory funnel
  2. extractionThe aqueous phase was extracted with DCM (2×40 mL)
  3. customSolvent was evaporated by rotavap
  4. customThe product was purified by preparative HPLC (acetonitrile/water−10 nM ammonium acetate)

Sources & evidence

ORD record
ord-10b10361865344b8ac840c5c10c79364
Source dataset
uspto-grants-2013_01
Patent number
US08362004B2

Reaction notes

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