Phenylacetylene → HCID 24957857, compound

HRID 2381826Notes

Reaction equation

C1(C#C)C=CC=CC=1.[C:9]1([CH2:15][C:16]#[CH:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[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:17]=[C:16]([CH2:15][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=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 575753Benzylacetylene

HCID 73213267HCID 73213267, compound

Product 1

HCID 24957857HCID 24957857, compoundYield 69%

Procedure

Following the procedure as described in Example 10, making variations as necessary to replace phenylacetylene with 3-phenyl-1-propyne to react with 2-azido-N-benzyl-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 69% yield: mp 139-141° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.99 (s, 1H), 7.35-7.28 (m, 10H), 6.29 (br s, 1H), 4.60 (t, J=6.0 Hz, 2H), 4.13 (s, 2H), 2.64 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 160.9, 155.5, 153.2, 149.1, 137.9, 137.5, 128.9, 128.8, 128.7, 127.8, 126.8, 124.1, 119.2, 44.3, 32.1, 17.3; MS (ES+) m/z 390.2 (M+1).

Sources & evidence

ORD record: ord-a37f44fc4b6246768484e5f4b8adfc24
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258160B2

Reaction notes

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