Phenylacetylene → HCID 24958599, compound

HRID 2381836Notes

Reaction equation

HRID 2381836 reaction equation
C1(C#C)C=CC=CC=1.[C:9]1([C@H:15]([OH:18])[C:16]#[CH:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH: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:17]=[C:16]([C@H:15]([OH:18])[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH: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 6993954(S)-1-Phenyl-2-propyn-1-olHCID 73213267HCID 73213267, compound

Product 1

HCID 24958599HCID 24958599, compoundYield 67%

Procedure

Following the procedure as described in Example 10, making variations as necessary to replace phenylacetylene with (R)-1-phenyl-2-propyn-1-ol to react with 2-azido-N-benzyl-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 67% yield: mp 146-149° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.12 (s, 1H), 7.50-7.31 (m, 10H), 6.13-6.08 (m, 2H), 4.61 (d, J=6.0 Hz, 2H), 2.96 (d, J=3.0 Hz, 1H), 2.64 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 160.8, 155.2, 152.9, 152.3, 140.9, 137.3, 128.8, 128.7, 128.2, 127.9, 127.7, 126.3, 124.5, 118.9, 68.9, 44.2, 17.2; MS (ES+) m/z 406.3 (M+1).

Sources & evidence

ORD record
ord-6c37d42aacf8456cba0becafad24a3ec
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

Loading…