Phenylacetylene → HCID 24958598, compound

HRID 2381835Notes

Reaction equation

HRID 2381835 reaction equation
C1(C#C)C=CC=CC=1.[C:9]([C:11]1[CH:15]=[CH:14][S:13][CH:12]=1)#[CH:10].[N:16]([C:19]1[S:20][C:21]([C:25]([NH:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])=[C:22]([CH3:24])[N:23]=1)=[N+:17]=[N-:18]>>[CH2:28]([NH:27][C:25]([C:21]1[S:20][C:19]([N:16]2[CH:10]=[C:9]([C:11]3[CH:15]=[CH:14][S:13][CH:12]=3)[N:18]=[N:17]2)=[N:23][C:22]=1[CH3:24])=[O:26])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 3

HCID 10821PhenylacetyleneHCID 35484223-EthynylthiopheneHCID 73213267HCID 73213267, compound

Product 1

HCID 24958598HCID 24958598, compoundYield 66%

Procedure

Following the procedure as described in Example 10, making variations as necessary to replace phenylacetylene with 3-ethynylthiophene to react with 2-azido-N-benzyl-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 66% yield: mp 123-126° C. (dichloromethane); 1H NMR (300 MHz, CDCl3) δ 8.49 (s, 1H), 7.82-7.81 (m, 1H), 7.51-7.32 (m, 7H), 6.11 (br s, 1H), 4.63 (d, J=6.0 Hz, 2H), 2.71 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 160.9, 155.4, 153.3, 144.8, 137.4, 130.3, 128.9, 127.9, 127.9, 126.8, 125.7, 124.4, 122.6, 116.4, 44.3, 17.4; MS (ES+) m/z 382.3 (M+1).

Sources & evidence

ORD record
ord-80d5cc65d3364dffa317733bf54f1b3a
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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