Phenylacetylene → HCID 24958231, compound

HRID 2381831Notes

Reaction equation

C1(C#C)C=CC=CC=1.[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=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:16]=[CH:15][CH:14]=[CH:13][N:12]=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

Reactant 3

HCID 10821Phenylacetylene

HCID 137268Ethynylpyridine

HCID 73213267HCID 73213267, compound

Product 1

HCID 24958231HCID 24958231, compoundYield 34%

Procedure

Following the procedure as described in Example 10, making variations as necessary to replace phenylacetylene with 2-ethynylpyridine to react with 2-azido-N-benzyl-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 34% yield: mp 184-187° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.96 (s, 1H), 8.65-8.63 (m, 1H), 8.21-8.19 (m, 1H), 7.84-7.79 (m, 1H), 7.39-7.27 (m, 6H), 6.13 (t, J=6.0 Hz, 1H), 4.64 (d, J=6.0 Hz, 2H), 2.71 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 160.9, 153.3, 149.8, 149.2, 149.0, 138.8, 137.4, 136.9, 128.9, 127.9, 127.8, 124.8, 123.5, 120.7, 119.4, 44.4, 17.5; MS (ES+) m/z 377.3 (M+1).

Sources & evidence

ORD record: ord-0d765c5172324d21a4615c75f010bd6a
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258160B2

Reaction notes

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