Propargyl bromide → 5-(2,4-dichlorophenyl)-3,6-diethyl-N-[(1R,2S)-2-(prop-2-ynyloxy)-2,3-dihydro-1H-inden-1-yl]pyrazin-2-amine
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([CH2:30][CH3:31])[C:12]([NH:17][C@@H:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][C@@H:19]2[O:27][CH2:28][CH3:29])=[N:13][C:14]=1[CH2:15][CH3:16].[CH2:32](Br)C#C>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([CH2:30][CH3:31])[C:12]([NH:17][C@@H:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][C@@H:19]2[O:27][CH2:28][C:29]#[CH:32])=[N:13][C:14]=1[CH2:15][CH3:16]Participants
3
Procedure
Following the procedure for the preparation of 5-(2,4-dichlorophenyl)-N-[(1R,2S)-2-ethoxy-2,3-dihydro-1H-inden-1-yl]-3,6-diethylpyrazin-2-amine but substituting propargylbromide and making non-critical variations provided the title compound as a white solid. IR (diffuse reflectance) 3451, 3293, 2964, 2932, 1563, 1493, 1469, 1390, 1204, 1184, 1087, 1076, 820, 742, 646 cm−1; OAMS supporting ions at: ESI+ 465.8; MS (EI) m/z 465 (M+); HRMS (FAB) calcd for C26H25CL2N3O+H1 466.1453, found 466.1455. [α]25D=−56 (c 0.83, methylene chloride). Anal. Calcd for C26H25Cl2N3O: C, 66.96; H, 5.40; N, 9.01. Found: C, 66.96; H, 5.49; N, 8.93.
Sources & evidence
- ORD record
- ord-8f2b8017f82f49a6946cd5d3da881f93
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07041672B2
Reaction notes
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