Triethylamine → 4-[cis-2,6-Dimethyl-4-(4-trifluoromethoxy-phenyl)-piperazine-1-sulfonyl]-indan-2-carbonitrile
Reaction equation
C(N(CC)CC)C.P(Cl)(Cl)(Cl)=O.[CH3:13][C@H:14]1[CH2:19][N:18]([C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=2)[CH2:17][C@@H:16]([CH3:31])[N:15]1[S:32]([C:35]1[CH:43]=[CH:42][CH:41]=[C:40]2[C:36]=1[CH2:37][CH:38]([C:44]([NH2:46])=O)[CH2:39]2)(=[O:34])=[O:33]>ClC(Cl)C>[CH3:13][C@H:14]1[CH2:19][N:18]([C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]([F:29])([F:28])[F:30])=[CH:22][CH:21]=2)[CH2:17][C@@H:16]([CH3:31])[N:15]1[S:32]([C:35]1[CH:43]=[CH:42][CH:41]=[C:40]2[C:36]=1[CH2:37][CH:38]([C:44]#[N:46])[CH2:39]2)(=[O:34])=[O:33]Participants
Procedure
Triethylamine (200 μL, 1.4349 mmol) and phosphorus oxychloride (74 μL, 0.7939 mmol) were added to a solution of 4-[cis-2,6-dimethyl-4-(4-trifluoromethoxy-phenyl)-piperazine-1-sulfonyl]-indan-2-carboxylic acid amide (254 mg, 0.5105 mmol) in dichloroethane (3 mL). The reaction was stirred for 4 h at room temperature then directly purified by silica gel column chromatography (0-50% EtOAc in hexanes) to afford 4-[cis-2,6-dimethyl-4-(4-trifluoromethoxy-phenyl)-piperazine-1-sulfonyl]-indan-2-carbonitrile (23 mg, 9%). 1H NMR (400 MHz, CD3OD) δ ppm 7.77 (d, 1H), 7.54 (d, 1H), 7.42 (t, 1H), 7.10 (d, 2H), 6.93 (d, 2H), 4.20-4.00 (m, 2H), 3.65-3.60 (m, 1H), 3.60-3.40 (m, 2H), 3.40-3.20 (m, 4H), 2.80-2.60 (m, 2H), 1.50 (d, 6H). LCMS: 480.0 (M+1)+.
Workup
- customthen directly purified by silica gel column chromatography (0-50% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-1d8460c783fe4b94a11eaf2cc147570a
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07834004B2
Reaction notes
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