Aniline → HCID 10384320, compound

HRID 1696902Notes

Reaction equation

HRID 1696902 reaction equation
CN(C(O[N:9]1N=N[C:11]2[CH:12]=[CH:13][CH:14]=[N:15][C:10]1=2)=[N+](C)C)C.[F:18][P-](F)(F)(F)(F)F.C([N:28]([CH:31](C)C)CC)(C)C.[NH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[CH2:41]([OH:48])[C:42](N)([CH2:45][OH:46])[CH2:43]O.C(=O)([O-])[O-].[CH3:53][C:54]([N:56]([CH3:58])C)=O>>[NH2:28][CH:31]1[CH2:53][CH2:54][N:56]([C:14]2[N:15]=[C:10]3[C:11]([C:41](=[O:48])[C:42]([C:45]([NH:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[O:46])=[CH:43][NH:9]3)=[CH:12][C:13]=2[F:18])[CH2:58]1

Participants

7

Reactant 6

HCID 6115AnilineHCID 6503Tris(hydroxymethyl)aminomethaneHCID 19660Carbonate IonHCID 31374DimethylacetamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 10384320HCID 10384320, compound

Procedure

A solution of EXAMPLE 11A (50 mg), hydroxyazobenzotriazole (20 mg), 0-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (50 mg), diisopropylethylamine (0.025 mL), N,N-dimethylaminopyridine (100 mg), and dimethylacetamide (2 mL) was stirred for 30 minutes, treated with aniline (12.6 mg), stirred for 18 hours, treated with trisamine resin (0.26 g), stirred for 2 hours, treated with carbonate resin (0.090 g), stirred for 2 hours, and filtered. The filtrate was concentrated, and the concentrate was dissolved in dichloromethane, applied to a silica gel-containing solid-phase extraction cartridge, and eluted with 25% ethyl acetate/hexanes then 10% methanol/dichloromethane. The product was dissolved in trifluoroacetic acid, stirred at 80° C. for 18 hours in a sealed vial, and concentrated. This concentrate was dissolved in methanol, treated with anion exchange resin, and filtered. The filtrate was concentrated, and the concentrate was purified by reverse phase HPLC. NMR (300 MHz, CD3OD) δ 8.65 (s, 1H), 8.05 (m, 1H), 7.60-7.70 (m, 2H), 7.30-7.40 (m, 2H), 7.10-7.15 (m, 1H), 3.85-4.15 (m, 5H), 2.40-2.55 (m, 1H), 2.10-2.50 (m, 1H).

Workup

  1. stirringstirred for 2 hours
  2. stirringstirred for 2 hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. dissolutionthe concentrate was dissolved in dichloromethane
  6. additioncontaining
  7. extractionsolid-phase extraction cartridge
  8. washeluted with 25% ethyl acetate/hexanes
  9. dissolutionThe product was dissolved in trifluoroacetic acid
  10. stirringstirred at 80° C. for 18 hours in a sealed vial, and
  11. concentrationconcentrated
  12. dissolutionThis concentrate was dissolved in methanol
  13. additiontreated with anion exchange resin
  14. filtrationfiltered
  15. concentrationThe filtrate was concentrated
  16. customthe concentrate was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-2608a44af61b40f1abdb9bf0e5d9fd6e
Source dataset
uspto-grants-2012_04
Patent number
US08163769B2

Reaction notes

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