Phenylacetylene → HCID 24958229, compound

HRID 2381829Notes

Reaction equation

C1(C#C)C=CC=CC=1.[CH2:9]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10]#[CH:11].[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:11]=[C:10]([CH2:9][O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=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 83613(Prop-2-ynyloxy)benzene

HCID 73213267HCID 73213267, compound

Product 1

HCID 24958229HCID 24958229, compoundYield 36%

Procedure

Following the procedure as described in Example 10, making variations as necessary to replace phenylacetylene with phenyl propargyl ether to react with 2-azido-N-benzyl-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 36% yield: mp 140-143° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.45 (s, 1H), 7.38-7.26 (m, 7H), 7.02-6.98 (m, 3H), 6.15 (t, J=6.0 Hz, 1H), 5.28 (s, 2H), 4.63 (d, J=6.0 Hz, 2H), 2.68 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 160.8, 157.9, 155.3, 153.2, 145.6, 137.4, 129.6, 128.9, 127.9, 127.9, 124.7, 121.5, 120.3, 114.7, 61.5, 44.4, 17.4; MS (ES+) m/z 406.3 (M+1).

Sources & evidence

ORD record: ord-397375e4b09149d3bf3d4b7fdb6e8316
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258160B2

Reaction notes

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