Phenylacetylene → HCID 24958597, compound

HRID 2381834Notes

Reaction equation

HRID 2381834 reaction equation
C1(C#C)C=CC=CC=1.[C:9]1([NH: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][NH: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

4

Reactant 3

HCID 10821PhenylacetyleneHCID 305815N-prop-2-ynylanilineHCID 73213267HCID 73213267, compound

Product 1

HCID 24958597HCID 24958597, compoundYield 18%

Procedure

Following the procedure as described in Example 10, making variations as necessary to replace phenylacetylene with phenyl prop-2-ynyl amine to react with 2-azido-N-benzyl-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 18% yield: mp 159-162° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.31 (s, 1H), 7.42-7.35 (m, 5H), 7.30-7.21 (m, 2H), 6.82-6.77 (m, 1H), 6.73-6.69 (m, 2H), 6.18 (t, J=6.0 Hz, 1H), 4.66 (d, J=6.0 Hz, 2H), 4.58 (d, J=6.0 Hz, 2H), 4.32 (br s, 1H), 2.70 (s, 3H); 13C NMR (75 MHz, CDCl3) 160.9, 155.4, 153.1, 147.7, 147.1, 137.4, 129.4, 128.9, 127.9, 127.9, 124.5, 119.3, 118.3, 113.1, 44.3, 39.6, 17.4; MS (ES+) m/z 405.3 (M+1).

Sources & evidence

ORD record
ord-9de7ce62b0034201968f563fda023d01
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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