Ammonia → HCID 178485288, compound

HRID 238555Notes

Reaction equation

HRID 238555 reaction equation
[N:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([N:10]([CH3:22])[C:11]([C:13]2[CH:21]=[CH:20][C:16]3=[N:17][O:18][N:19]=[C:15]3[CH:14]=2)=[O:12])[CH2:6][CH2:5]1)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N>N1C=CC=CC=1>[NH2:1][C@H:4]1[CH2:9][CH2:8][C@H:7]([N:10]([CH3:22])[C:11]([C:13]2[CH:21]=[CH:20][C:16]3=[N:17][O:18][N:19]=[C:15]3[CH:14]=2)=[O:12])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 11776TriphenylphosphineHCID 178485289HCID 178485289, compound

Product 1

HCID 178485288HCID 178485288, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-(trans-4-Azidocyclohexyl)-N-methyl-[2,1,3]-benzoxadiazole-5-carboxamide (0.18 g, 0.6 mmol) was dissolved in pyridine (4 ml), Ph3P (0.26 g, 1.0 mmol) was added, and the mixture stirred for 1 hour at room temperature. Conc. ammonia solution (6 ml) was slowly added and the mixture stirred for 2 h at 20° C. before evaporating under vacuum and purifying the crude product on silica gel, eluting with chloroform/methanol/triethylamine (90:10:1), to give a white solid after trituration with diethyl ether (0.067 g). Mp=145-146° C., 1H NMR (300 MHz, DMSO+CDCl3, rotamers) δ 7.93 (d, J=8.7 Hz, 1H); 7.82 (s, 1H); 7.41 (d, J=8.7 Hz, 1H); 4.60-4.50 and 3.55-3.35 and 2.80-2.55 (m, 2H); 3.00 and 2.88 (s+s, 3H); 2.10-0.90 ppm (s, 8H).

Workup

  1. stirringthe mixture stirred for 2 h at 20° C.
  2. custombefore evaporating under vacuum
  3. custompurifying the crude product on silica gel
  4. washeluting with chloroform/methanol/triethylamine (90:10:1)
  5. customto give a white solid after trituration with diethyl ether (0.067 g)

Sources & evidence

ORD record
ord-fa1c5538ca7a447197360c9ca611d829
Source dataset
uspto-grants-2014_02
Patent number
US08642633B2

Reaction notes

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