Diisopropylethylamine → HCID 46861573, compound
Reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]([C:16]3[N:20]4[CH:21]=[C:22]([S:25][C:26]5[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=5)[CH:23]=[CH:24][C:19]4=[N:18][N:17]=3)[CH:13]=[CH:14][CH:15]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.ClC(Cl)(Cl)C[O:36][C:37]([NH:39][C:40]1[N:44]([C:45]2[CH:50]=[CH:49][C:48]([CH3:51])=[CH:47][CH:46]=2)[N:43]=[C:42]([C:52]([CH3:55])([CH3:54])[CH3:53])[CH:41]=1)=O.CCN(C(C)C)C(C)C>CS(C)=O>[C:52]([C:42]1[CH:41]=[C:40]([NH:39][C:37]([NH:32][C:29]2[CH:28]=[CH:27][C:26]([S:25][C:22]3[CH:23]=[CH:24][C:19]4[N:20]([C:16]([C:12]5[CH:13]=[CH:14][CH:15]=[C:10]([O:9][CH2:8][CH2:7][N:1]6[CH2:2][CH2:3][O:4][CH2:5][CH2:6]6)[CH:11]=5)=[N:17][N:18]=4)[CH:21]=3)=[CH:31][CH:30]=2)=[O:36])[N:44]([C:45]2[CH:50]=[CH:49][C:48]([CH3:51])=[CH:47][CH:46]=2)[N:43]=1)([CH3:55])([CH3:53])[CH3:54]Participants
Procedure
A mixture of Example 10 step c (315 mg, 0.703 mmol), 5-(2,2,2-trichloroethoxycarbonyl)amino-3-tert-butyl-1-p-tolyl-1H-pyrazole (299 mg, 0.703 mmol) and DIPEA (116 μL, 0.675 mmol) in DMSO (3 mL) was heated at 55° C. for 24 h. The reaction was concentrated in vacuo and the residue purified by reverse phase preparative HPLC (Method 3) to afford the title compound (202 mg, 41%) as an off-white solid. LCMS (Method 4): Rt 8.46 min, m/z 703 [MH+]. 1H NMR (400 MHz, CDCl3): δ 9.30 (1 H, br s), 8.34 (1 H, br s), 8.16 (1 H, s), 7.49-7.41 (3 H, m), 7.37 (1 H, d, J 9.6), 7.29 (2 H, d, J 8.4), 7.25-7.20 (2 H, m), 7.18 (2 H, d, J 8), 7.09-7.04 (2 H, m), 6.90 (2 H, d, J 8), 6.44 (1 H, s), 4.15 (2 H, t, J 5.4), 3.72 (4 H, t, J 4.5), 2.88 (2 H, t, J 5.4), 2.64 (4 H, t, J 4.4), 2.11 (3 H, s), 1.30 (9 H, s).
Workup
- concentrationThe reaction was concentrated in vacuo
- customthe residue purified by reverse phase preparative HPLC (Method 3)
Sources & evidence
- ORD record
- ord-8387c50fcae641ffa9567b998094175e
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08557797B2
Reaction notes
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