Phenylacetylene → HCID 178516875, compound

HRID 539540Notes

Reaction equation

HRID 539540 reaction equation
[C:1]1([C:7]#C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N([CH2:12]CCC1C=CNC(=O)C=1OCC1C=CC=CC=1)=[N+]=[N-].[C:30]1([N:36]2[CH:41]=[CH:40][C:39]([CH2:42][CH2:43][C:44]3[N:45]=[N:46][NH:47][CH:48]=3)=[C:38]([O:49]C)[C:37]2=[O:51])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[C:30]1([N:36]2[CH:41]=[CH:40][C:39]([CH2:42][CH2:43][CH2:44][C:48]3[N:47]=[N:46][NH:45][CH:12]=3)=[C:38]([O:49][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:37]2=[O:51])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 3

HCID 10821PhenylacetyleneHCID 71139397(3-Azidopropyl)-3-benzyloxypyridine-2-oneHCID 178488794HCID 178488794, compound

Product 1

HCID 178516875HCID 178516875, compoundYield 77%

Procedure

Reaction of phenylacetylene (0.127 g, 1.25 mmol) and 157b (0.295 g, 1.04 mmol) within 4 h as described for synthesis of 158a gave compound 158b (0.31 g, 77%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.00 (s, 1H), 7.77 (d, J=7.3 Hz, 2H), 7.27 (m, 8H), 6.88 (d, J=5.7 Hz, 1H), 6.57 (d, J=6.4 Hz, 1H), 5.95 (t, J=7.1 Hz, 1H), 4.99 (s, 2H), 4.34 (t, J=6.4 Hz, 2H), 3.94 (t, J=6.4 Hz, 2H), 2.32 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 157.92, 148.47, 147.30, 135.73, 130.26, 128.81, 128.49, 128.22, 127.76, 127.71, 127.01, 125.33, 120.16, 114.95, 104.83, 70.33, 47.00, 46.48, 29.30. HRMS (EI) calcd for C23H22N4O2 [M]+ 386.1743. found 386.1734.

Sources & evidence

ORD record
ord-8f58910575c04122801c3e37cf6fd0a1
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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