Dimethylformamide → HCID 86594878, compound

HRID 1354722Notes

Reaction equation

HRID 1354722 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-1df1d2da807c4e6b9314053419835b8d
Source dataset
uspto-grants-2007_05
Patent number
US07223788B2

Reaction notes

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