Phenylacetylene → HCID 24958600, compound

HRID 2381837Notes

Reaction equation

C1(C#C)C=CC=CC=1.[C:9]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)#[CH:10].[N:18]([C:21]1[S:22][C:23]([C:27]([NH:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])=[C:24]([CH3:26])[N:25]=1)=[N+:19]=[N-:20]>>[CH2:30]([NH:29][C:27]([C:23]1[S:22][C:21]([N:18]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:20]=[N:19]2)=[N:25][C:24]=1[CH3:26])=[O:28])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

Reactant 3

HCID 10821Phenylacetylene

HCID 5226271-Ethynyl-4-fluorobenzene

HCID 73213267HCID 73213267, compound

Product 1

HCID 24958600HCID 24958600, compoundYield 8%

Procedure

Following the procedure as described in Example 10, making variations as necessary to replace phenylacetylene with 1-ethynyl-4-fluorobenzene to react with 2-azido-N-benzyl-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 8% yield: mp 203-205° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.77-8.75 (m, 1H), 8.36-8.31 (m, 1H), 7.41-7.16 (m, 8H), 6.10 (br s, 1H), 4.64 (d, J=6.0 Hz, 2H), 2.72 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 161.13, 153.3, 142.3, 137.4, 130.3, 130.2, 129.0, 128.9, 128.2, 128.1, 127.9, 127.9, 124.8, 124.7, 119.8, 119.7, 116.1, 115.8, 44.4, 17.5; MS (ES+) m/z 394.3 (M+1).

Sources & evidence

ORD record: ord-dafde6eb2a564eaaa29007d5ef6af850
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258160B2

Reaction notes

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