Phenylacetylene → HCID 178516878, compound

HRID 539543Notes

Reaction equation

HRID 539543 reaction equation
[C:1]1([C:7]#C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:9]([CH2:12][CH2:13][CH2:14][CH2:15]CCN1C=CC=C(OCC2C=CC=CC=2)C1=O)=[N+:10]=[N-:11].[C:33]1([N:39]2[CH:44]=[CH:43][C:42]([CH2:45][CH2:46][C:47]3N=NN[CH:51]=3)=[C:41]([O:52]C)[C:40]2=[O:54])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[C:33]1([N:39]2[CH:44]=[CH:43][C:42]([CH2:45][CH2:46][CH2:47][CH2:51][CH2:15][CH2:14][C:13]3[N:11]=[N:10][NH:9][CH:12]=3)=[C:41]([O:52][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:40]2=[O:54])[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

4

Reactant 3

HCID 10821PhenylacetyleneHCID 711398441-(6-Azidohexyl)-3-benzyloxypyridine-2-oneHCID 178488794HCID 178488794, compound

Product 1

HCID 178516878HCID 178516878, compoundYield 56%

Procedure

Reaction of phenylacetylene (0.80 g, 0.78 mmol) and 157e (0.21 g, 0.65 mmol) within 4 h as described for synthesis of 158a gave compound 158e (0.16 g, 56%) as a white solid. NMR (400 MHz, CDCl3) δ 7.66 (m, 3H), 7.20 (m, 8H), 6.68 (dd, J=6.9, 1.5 Hz, 1H), 6.46 (dd, J=7.4, 1.5 Hz, 1H), 5.82 (t, J=7.1 Hz, 1H), 4.92 (s, 2H), 4.18 (t, J=6.8 Hz, 2H), 3.75 (t, J=6.8 Hz, 2H), 1.76 (m, 2H), 1.56 (m, 2H), 1.19 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 157.64, 148.46, 147.27, 135.95, 130.36, 128.57, 128.48, 128.19, 127.72, 127.60, 126.96, 125.32, 119.37, 115.02, 104.37 70.45, 50.03, 49.35, 29.90, 28.66, 25.87, 25.78. HRMS (FAB) calcd for C26H29N4O2 [M+H]+ 429.2290. found 429.2291.

Sources & evidence

ORD record
ord-5f676fe6c6974fd09b8a4409de2254ba
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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