Triethylamine → 3-(3-{[(4-Pyrazin-2-yl-benzyl)-(thiazole-2-sulfonyl)-amino]-methyl}-phenyl)-propionic acid methyl ester
Reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[S:6](Cl)(=[O:8])=[O:7].C(N(CC)CC)C.[CH3:17][O:18][C:19](=[O:43])[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][NH:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]3[CH:42]=[N:41][CH:40]=[CH:39][N:38]=3)=[CH:33][CH:32]=2)[CH:23]=1>>[CH3:17][O:18][C:19](=[O:43])[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][N:29]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]3[CH:42]=[N:41][CH:40]=[CH:39][N:38]=3)=[CH:33][CH:32]=2)[S:6]([C:2]2[S:1][CH:5]=[CH:4][N:3]=2)(=[O:8])=[O:7])[CH:23]=1Participants
4
Procedure
The title compound of Step A was prepared following the method dissolved in Step A of Example 1 from 3-{3-[(4-pyrazin-2-yl-benzylamino)-methyl]-phenyl}-propionic acid methyl ester, prepared in Step A of Example 11a, and thiazole-2-sulfonyl chloride using triethylamine in place of N,N-diisopropylethylamine. 1H NMR (400 MHz, CDCl3) δ 8.98 (s, 1H), 8.61 (s, 1H), 8.50 (s, 1H), 7.96 (d, 1H), 7.88 (d, 2H), 7.60 (d, 1H), 7.26 (d, 2H), 7.13 (m, 1H), 7.04 (m, 1H), 6.95 (m, 1H), 6.91 (s, 1H), 4.54 (s, 2H), 4.48 (s, 2H), 3.64 (s, 3H), 2.81 (t, 2H), 2.52 (t, 2H); MS 509 (M+1).
Sources & evidence
- ORD record
- ord-8310fb6a3b2a4fea96395668f336fbe5
- Source dataset
- uspto-grants-2002_12
- Patent number
- US06498172B1
Reaction notes
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