p-(Trifluoromethoxy)benzenesulphonyl chloride → N-{[1-methyl-3-phenyl-5-({[4-(trifluoromethoxy)phenyl]sulfonyl}amino)-1H-indol-2-yl]carbonyl}-L-leucine
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([C:12]([NH:14][C@H:15]([C:20]([O:22]C)=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18])=[O:13])=[C:5]2[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[F:30][C:31]([F:44])([F:43])[O:32][C:33]1[CH:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[CH:35][CH:34]=1>>[CH3:11][N:7]1[C:8]2[C:4](=[CH:3][C:2]([NH:1][S:39]([C:36]3[CH:37]=[CH:38][C:33]([O:32][C:31]([F:44])([F:43])[F:30])=[CH:34][CH:35]=3)(=[O:41])=[O:40])=[CH:10][CH:9]=2)[C:5]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:6]1[C:12]([NH:14][C@H:15]([C:20]([OH:22])=[O:21])[CH2:16][CH:17]([CH3:18])[CH3:19])=[O:13]Participants
3
Procedure
The title compound was prepared from methyl N-[(5-amino-1-methyl-3-phenyl-1H-indol-2-yl)carbonyl]-L-leucinate and 4-trifluoromethoxybenzenesulfonyl chloride followed the procedure of Example 1 Step 3 as a brown solid: 1H NMR (DMSO-d6) δ 0.79 (d, J=6.3 Hz, 3H, 0.80 (d, J=6.3 Hz, 3H, 1.35-1.60 (m, 3H, 3.75 (s, 3H, 4.25-4.35 (m, 1H, 7.03 (dd, J=8.8, 2.0 Hz, 1H, 7.24 (d, J=1.4 Hz, 1H, 7.25-7.40 (m, 5H, 7.47 (d, J=8.9 Hz, 1H, 7.55 (d, J=7.9 Hz, 2H, 7.77 (d, J=7.9 Hz, 2H, 8.77 (d, J=7.9 Hz, 1H, 9.99 (s, 1H, 12.64 (br s, 1H; MS (ESI) m/z 604 (MH+), MS (ESI) m/z 602 [M-H]−; HRMS calcd for C29H29F3N3O6S: 604.1727; found (ESI+): 604.1716; Anal. calcd for C29H28F3N3O6S.0.4H2O: C, 57.02; H, 4.75; N, 6.96. Found: C, 56.70; H, 4.75; N, 6.94.
Sources & evidence
- ORD record
- ord-8a0b38b688904651ab2fe44aa28d3fc3
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07442805B2
Reaction notes
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