Phenylacetylene → HCID 24958230, compound

HRID 2381830Notes

Reaction equation

HRID 2381830 reaction equation
C1(C#C)C=CC=CC=1.[C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)#[CH:10].[N:19]([C:22]1[S:23][C:24]([C:28]([NH:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])=[C:25]([CH3:27])[N:26]=1)=[N+:20]=[N-:21]>>[CH2:31]([NH:30][C:28]([C:24]1[S:23][C:22]([N:19]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[N:21]=[N:20]2)=[N:26][C:25]=1[CH3:27])=[O:29])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

4

Reactant 3

HCID 10821PhenylacetyleneHCID 2510201-Ethynyl-4-methoxybenzeneHCID 73213267HCID 73213267, compound

Product 1

HCID 24958230HCID 24958230, compoundYield 45%

Procedure

Following the procedure as described in Example 10, making variations as necessary to replace phenylacetylene with 4-ethynylanisole to react with 2-azido-N-benzyl-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 45% yield: mp 168-171° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.50 (s, 1H), 7.82 (d, J=8.8 Hz, 2H), 7.38-7.32 (m, 5H), 6.99 (d, J=8.8 Hz, 2H), 6.13 (br s, 1H), 4.63 (d, J=6.0 Hz, 2H), 3.86 (s, 3H), 2.71 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 160.9, 160.2, 155.5, 153.3, 148.6, 137.4, 128.9, 127.9, 127.9, 127.4, 124.2, 121.8, 115.8, 114.4, 55.4, 44.4, 17.4; MS (ES+) m/z 406.30 (M+1).

Sources & evidence

ORD record
ord-7ce194f250654bd883d02932d6573b73
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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