1,2,3,6-Tetrahydropyridine → 1-(1,3-Benzoxazol-6-ylcarbonyl)-1,2,3,6-tetrahydropyridine

HRID 442642Notes

Reaction equation

HRID 442642 reaction equation
[O:1]1[C:5]2[CH:6]=[C:7]([C:10]([OH:12])=O)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[NH:13]1[CH2:18][CH:17]=[CH:16][CH2:15][CH2:14]1.C(C1NC=CN=1)(C1NC=CN=1)=O.C(Cl)(=O)C(Cl)=O>>[O:1]1[C:5]2[CH:6]=[C:7]([C:10]([N:13]3[CH2:14][CH:15]=[CH:16][CH2:17][CH2:18]3)=[O:12])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 4

HCID 127501,2,3,6-TetrahydropyridineHCID 65578Oxalyl chlorideHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 222459381,3-Benzoxazole-6-carboxylic acid

Product 1

HCID 115359401-(1,3-Benzoxazol-6-ylcarbonyl)-1,2,3,6-tetrahydropyridine

Procedure

Coupling of 1,3-benzoxazol-6-carboxylic acid with 1,2,3,6-tetrahydropyridine is performed in the same manner as described for the preparation of Invention Compound V through activation with carbonyl diimidazole or by activation with other suitable reagents such as oxalyl chloride. The product can be isolated by the same methods as described for the isolation of Invention Compound V and purified by chromatography on silica gel. EIMS m/z=228 (parent), 146 (base), and 118. 1H NMR δ 2.2 (br, 2), 3.4-4.3 (br m, 4), 5.7-5.95 (br m, 2), 7.52 (dd, 1, J=8.39, 1.49 Hz), 7.64 (d, 1, J=8.41 Hz), 7.87 (d, 1, J=1.32 Hz), and 8.16 ppm (s, 1).

Workup

  1. customThe product can be isolated by the same methods
  2. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-7b06e1cf9a5e4616abe2c06d9171acd0
Source dataset
uspto-grants-1999_04
Patent number
US05891876

Reaction notes

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