Phenylacetylene → HCID 24958596, compound

HRID 2381833Notes

Reaction equation

HRID 2381833 reaction equation
C1(C#C)C=CC=CC=1.[C:9]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)#[CH:10].[N:17]([C:20]1[S:21][C:22]([C:26]([NH:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])=[C:23]([CH3:25])[N:24]=1)=[N+:18]=[N-:19]>>[CH2:29]([NH:28][C:26]([C:22]1[S:21][C:20]([N:17]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)[N:19]=[N:18]2)=[N:24][C:23]=1[CH3:25])=[O:27])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 3

HCID 10821PhenylacetyleneHCID 1860033-EthynylpyridineHCID 73213267HCID 73213267, compound

Product 1

HCID 24958596HCID 24958596, compoundYield 13%

Procedure

Following the procedure as described in Example 10, making variations as necessary to replace phenylacetylene with 3-ethynylpyridine to react with 2-azido-N-benzyl-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 13% yield: mp 117-119° C. (methanol/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 9.65 (s, 1H), 9.04 (t, J=3.0 Hz, 1H), 8.42 (d, J=6.0 Hz, 1H), 7.71 (d, J=6.0 Hz, 1H), 7.39-7.27 (m, 7H), 4.48 (d, J=6.0 Hz, 2H), 2.66 (s, 3H); MS (ES+) m/z 377.3 (M+1).

Sources & evidence

ORD record
ord-ba35036d5d8e4406960eee371627d523
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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