Dimethylformamide → HCID 86594878, compound

HRID 2426668Notes

Reaction equation

HRID 2426668 reaction equation
CN(C([O:8]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:25]1[CH:26]=[CH:27][C:28]2[N:33](O)N=N[C:29]=2[CH:30]=1.[F:35][C:36]1[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:37]=1[C:43]1[CH:48]=[CH:47][C:46](C(O)=O)=[CH:45][CH:44]=1.NC1C=[CH:57][C:56]([N:59]2C[CH2:62][CH:61](N(C)C(=O)C)[CH2:60]2)=[CH:55][CH:54]=1.C[N:70]([CH:72]=[O:73])C>C(N(CC)CC)C>[C:61]([CH2:60][NH:59][CH:56]1[CH2:55][CH2:54][N:33]([C:28]2[CH:27]=[CH:26][C:25]([NH:70][C:72]([C:46]3[CH:45]=[CH:44][C:43]([C:37]4[CH:38]=[CH:39][C:40]([F:42])=[CH:41][C:36]=4[F:35])=[CH:48][CH:47]=3)=[O:73])=[CH:30][CH:29]=2)[CH2:57]1)(=[O:8])[CH3:62]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 27582644-(2,4-difluorophenyl)benzoic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21105566N-[1-(4-aminophenyl)pyrrolidin-3-yl]-N-methylacetamide

Product 1

HCID 86594878HCID 86594878, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

0.095 g of HATU, 0.068 g of HOBT and 0.035 ml of triethylamine were added to a solution of 0.047 g of 2′,4′-difluorobiphenyl-4-carboxylic acid and 0.058 g of N-[1-(4-aminophenyl)pyrrolidin-3-yl]-N-methylacetamide in 2 ml of DMF at 0° C. After 10 minutes, the solution was allowed to reach room temperature and was stirred at this temperature overnight. The solvent was then removed in vacuo, and the residue was taken up in water/ethyl acetate. The ethyl acetate phase was washed with 10% NaHCO3 solution and water. The ethyl acetate phase was dried over sodium sulfate, and the solvent was removed in vacuo. The residue was purified by preparative HPLC. The desired product was obtained. Molecular weight 449.19 (C26H25F2N3O2), MS: 450 (M+H+).

Workup

  1. customto reach room temperature
  2. customThe solvent was then removed in vacuo
  3. washThe ethyl acetate phase was washed with 10% NaHCO3 solution and water
  4. dry with materialThe ethyl acetate phase was dried over sodium sulfate
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-357dcd0cf21b4d528811431c0e13a5af
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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