Dimethylformamide → HCID 19921775, compound

HRID 1647757Notes

Reaction equation

HRID 1647757 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:22]([OH:24])=[O:23])=[N:14]1.C(N(CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:39])C=CC=CC=1.CN(C)[CH:51]=[O:52]>ClCCl.C(OCC)(=O)C>[C:51]([OH:52])(=[O:39])/[CH:16]=[CH:15]/[C:22]([OH:24])=[O:23].[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:22]([N:10]2[CH2:11][CH2:12][CH:7]([C:3]3[N:4]=[CH:5][NH:6][C:2]=3[CH3:1])[CH2:8][CH2:9]2)=[O:23])=[N:14]1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 78250Indazole-3-carboxylic acidHCID 199401P,P-Diphenylphosphinic azideHCID 10953883HCID 10953883, compound

Product 1

HCID 19921775HCID 19921775, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 100-ml round-bottomed flask, 1.35 g (8.15 mmol) of 4-(5-methyl-1H-imidazol-4-yl)piperidine are placed in 15 ml of dichloromethane and 4 ml of dimethylformamide. 1.32 g (8.15 mmol) of 1H-indazole-3-carboxylic acid and 2.2 ml of triethylamine are added. The mixture is left stirring for 5 minutes. 3.5 ml of diphenylphosphoryl azide are added and the mixture is left stirring for 72 hours. Ethyl acetate is added and the mixture is extracted 3 times with 2N hydrochloric acid. The aqueous phase is recovered and alkalinized with sodium carbonate solution. It is extracted 3 times with ethyl acetate and the organic phase is collected, dried and evaporated to dryness. The residue is purified by chromatography on a column of silica gel, eluting with a dichloromethane/methanol/ammonia solution (90:10:1) mixture.

Workup

  1. waitThe mixture is left
  2. waitthe mixture is left
  3. stirringstirring for 72 hours
  4. extractionthe mixture is extracted 3 times with 2N hydrochloric acid
  5. customThe aqueous phase is recovered
  6. extractionIt is extracted 3 times with ethyl acetate
  7. customthe organic phase is collected
  8. customdried
  9. customevaporated to dryness
  10. customThe residue is purified by chromatography on a column of silica gel
  11. washeluting with a dichloromethane/methanol/ammonia solution (90:10:1) mixture

Sources & evidence

ORD record
ord-dde07ab0a8454840b7ac8d583d3f0b2f
Source dataset
uspto-grants-1995_07
Patent number
US05434169

Reaction notes

Loading…