Phenylacetylene → HCID 24957858, compound

HRID 2381827Notes

Reaction equation

C1(C#C)C=CC=CC=1.[C:9]1([CH2:15][CH2:16][C:17]#[CH:18])[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:18]=[C:17]([CH2:16][CH2:15][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

Reactant 3

HCID 10821Phenylacetylene

HCID 1233604-Phenyl-1-butyne

HCID 73213267HCID 73213267, compound

Product 1

HCID 24957858HCID 24957858, compoundYield 20%

Procedure

Following the procedure as described in Example 10, making variations as necessary to replace phenylacetylene with 4-phenyl-1-butyne to react with 2-azido-N-benzyl-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 20% yield: mp 167-170° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.02 (s, 1H), 7.37-7.19 (m, 10H), 6.15 (t, J=6.0 Hz, 1H), 4.62 (d, J=6.0 Hz, 2H), 3.14-3.02 (m, 4H), 2.67 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 160.9, 155.6, 153.3, 148.5, 140.5, 137.5, 128.9, 128.5, 128.3, 127.8, 126.3, 124.0, 118.6, 44.3, 35.0, 27.2, 17.4; MS (ES+) m/z 404.3 (M+1).

Sources & evidence

ORD record: ord-907df00b741d4275b78587c78b6dd8b2
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258160B2

Reaction notes

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