Phenylacetylene → HCID 24958601, compound

HRID 2381838Notes

Reaction equation

HRID 2381838 reaction equation
C1(C#C)C=CC=CC=1.[CH:9]1([CH2:15][CH2:16][C:17]#[CH:18])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[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:18]=[C:17]([CH2:16][CH2:15][CH:9]3[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]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 15172911(But-3-yn-1-yl)cyclohexaneHCID 73213267HCID 73213267, compound

Product 1

HCID 24958601HCID 24958601, compoundYield 22%

Procedure

Following the procedure as described in Example 10, making variations as necessary to replace phenylacetylene with 4-cyclohexylbutyne to react with 2-azido-N-benzyl-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 22% yield: mp 82-84° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.10 (s, 1H), 7.37-7.33 (m, 5H), 6.19 (br s, 1H), 4.62 (d, J=6.0 Hz, 2H), 2.79 (t, J=6.0 Hz, 2H), 2.68 (s, 3H), 1.78-1.56 (m, 5H), 1.30-1.16 (m, 5H), 0.99-0.71 (m, 3H); 13C NMR (75 MHz, CDCl3) δ 160.9, 155.7, 153.3, 149.9, 137.5, 128.8, 127.8, 123.8, 118.2, 44.3, 37.0, 36.5, 33.1, 26.5, 26.2, 22.9, 17.4; MS (ES+) m/z 410.4 (M+1).

Sources & evidence

ORD record
ord-4d271ac99b2544d49c17ebf7bb8d567d
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

Loading…