Phenylacetylene → HCID 24958228, compound

HRID 2381828Notes

Reaction equation

HRID 2381828 reaction equation
C1(C#C)C=CC=CC=1.[C:9]1([CH2:15][CH2:16][CH2:17][C:18]#[CH:19])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[N:20]([C:23]1[S:24][C:25]([C:29]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])=[C:26]([CH3:28])[N:27]=1)=[N+:21]=[N-:22]>>[CH2:32]([NH:31][C:29]([C:25]1[S:24][C:23]([N:20]2[CH:19]=[C:18]([CH2:17][CH2:16][CH2:15][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:22]=[N:21]2)=[N:27][C:26]=1[CH3:28])=[O:30])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

4

Reactant 3

HCID 10821PhenylacetyleneHCID 745735-Phenyl-1-pentyneHCID 73213267HCID 73213267, compound

Product 1

HCID 24958228HCID 24958228, compoundYield 32%

Procedure

Following the procedure as described in Example 10, making variations as necessary to replace phenylacetylene with 5-phenyl-1-pentyne to react with 2-azido-N-benzyl-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 32% yield: mp 94-97° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.12 (s, 1H), 7.38-7.18 (m, 10H), 6.14 (t, J=6.0 Hz, 1H), 4.62 (d, J=6.0 Hz, 2H), 2.81 (t, J=9.0 Hz, 2H), 2.79-2.68 (m, 5H), 2.09-2.04 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 160.9, 155.7, 153.3, 149.2, 141.5, 137.4, 128.9, 128.4, 128.3, 127.9, 127.8, 125.9, 123.9, 118.4, 44.3, 35.2, 30.6, 24.9, 17.4; MS (ES+) m/z 418.3 (M+1).

Sources & evidence

ORD record
ord-05bf986a5b124501b20617603eb8ab94
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

Loading…