2-Bromoethyl methyl ether → 5-(2,4-dichlorophenyl)-3,6-diethyl-N-[(1R,2S)-2-(2-methoxyethoxy)-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].BrC[CH2:34][O:35]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][CH2:29][O:35][CH3:34])=[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-bromoethylmethylether and making non-critical variations provided the title compound as a light yellow syrup. IR (liq.) 3418, 2971, 2934, 2875, 1565, 1552, 1498, 1471, 1392, 1376, 1201, 1183, 1132, 1100, 748 cm−1; OAMS supporting ions at: ESI+ 485.8; MS (CI) m/z 486 (MH+); [α]25D=−102 (c 0.57, methylene chloride); Anal. Calcd for C26H29Cl2N3O2: C, 64.20; H, 6.01; N, 8.64. Found: C, 63.92; H, 6.14; N, 8.53.
Sources & evidence
- ORD record
- ord-5757847aada2431ab803ee0716a3a6f0
- Source dataset
- uspto-grants-2006_01
- Patent number
- US06992087B2
Reaction notes
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