4-(Trifluoromethyl)benzylamine → HCID 18922796, compound
Reaction equation
C(O[C:4]1[C:5](=[O:14])[C:6](=[O:13])[C:7]=1[NH:8][C:9]([CH3:12])([CH3:11])[CH3:10])C.[F:15][C:16]([F:26])([F:25])[C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH2:22])=[CH:19][CH:18]=1.[K+].[Br-]>>[C:9]([NH:8][C:7]1[C:6](=[O:13])[C:5](=[O:14])[C:4]=1[NH:22][CH2:21][C:20]1[CH:19]=[CH:18][C:17]([C:16]([F:15])([F:25])[F:26])=[CH:24][CH:23]=1)([CH3:10])([CH3:11])[CH3:12]Participants
Procedure
The title compound was prepared according to the procedure for example 1step 2 except that 3-ethoxy-4-(tert-butylamino)-cyclobut-3-ene-1,2-dione was used in place of (R)-3-ethoxy-4-(1,2,2-trimethyl-propylamino)-cyclobut-3-ene-1,2-dione and 4-trifluoromethyl-benzylamine was used in place of 4-fluoro-benzylamine. Yield: 63%; mp: 306-308° C.; 1H NMR (300 MHz, DMSO-d6): δ1.37 (m, 9H), 4.81-4.87 (m 2H), 7.57 (d, J=7.9 Hz, 2H), 7.76 (d, J=8.0 Hz, 2H), 7.81 (brm, 1H), one N--H proton not seen; IR (KBr, cm-1): 3291s, 3244s, 3061w, 2980m, 1794m, 1656s, 1567s, 1540s, 1471s, 1327s, 1162s, 1127s; MS (ES) m/z (relative intensity): 349 (M+ +Na, 20), 327 (M+ +H, 100); Anal. Calcd. for C16H17F3 N2O2 : C, 58.89; H, 5.25; N, 8.58. Found: C, 59.07; H, 5.34; N, 8.31.
Sources & evidence
- ORD record
- ord-0417cca18efd43c7854652770aee9c71
- Source dataset
- uspto-grants-1998_05
- Patent number
- US05750574
Reaction notes
Loading…