Isopropyl iodide → 5-(2,4-dichlorophenyl)-3,6-diethyl-N-[(1R,2S)-2-isopropoxy-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].I[CH:33](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][CH:28]([CH3:33])[CH3:29])=[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 2-iodopropane (20 equivalents iodide and sodium hydride with portion-wise addition) provided the title compound as a light yellow syrup. IR (liq.) 2971, 2935, 1564, 1552, 1497, 1471, 1392, 1379, 1368, 1206, 1177, 1140, 1123, 1101, 1061 cm−1; OAMS supporting ions at: ESI+ 470.2; MS (EI) m/z 469 (M+); HRMS (FAB) calcd for C26H29CL2N3O+H1 470.1766, found 470.1773. [α]25D=−93 (c 0.33, methylene chloride); Anal. Calcd for C26H29Cl2N3O: C, 66.38; H, 6.21; N, 8.93. Found: C, 66.53; H, 6.19; N, 8.89.
Sources & evidence
- ORD record
- ord-cb1af69855d5447c8593fff85d74ee39
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07041672B2
Reaction notes
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