Phenylacetylene → HCID 24958232, compound

HRID 2381832Notes

Reaction equation

HRID 2381832 reaction equation
C1(C#C)C=CC=CC=1.[C:9]1([CH: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]([CH: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 20155alpha-EthynylbenzenemethanolHCID 73213267HCID 73213267, compound

Product 1

HCID 24958232HCID 24958232, compoundYield 65%

Procedure

Following the procedure as described in Example 10, making variations as necessary to replace phenylacetylene with 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 65% yield: mp 143-146° C. (methanol/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.12 (s, 1H), 7.49-7.28 (m, 10H), 6.19 (t, J=6.0 Hz, 1H), 6.07 (d, J=6.0 Hz, 1H), 4.60 (d, J=6.0 Hz, 2H), 3.11 (d, J=3.0 Hz, 1H), 2.63 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 160.9, 155.4, 153.1, 152.4, 141.1, 137.4, 128.9, 128.8, 128.4, 127.9, 127.9, 126.4, 124.6, 119.0, 69.1, 44.3, 17.3; MS (ES+) m/z 406.3 (M+1).

Sources & evidence

ORD record
ord-4ddf2f350f8d4e899fbdcb86435f7e3c
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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