3-(Trifluoromethyl)benzylamine → HCID 18922799, 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:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20][NH2:21].[K+].[Br-]>>[C:9]([NH:8][C:7]1[C:6](=[O:13])[C:5](=[O:14])[C:4]=1[NH:21][CH2:20][C:19]1[CH:22]=[CH:23][CH:24]=[C:17]([C:16]([F:15])([F:25])[F:26])[CH:18]=1)([CH3:10])([CH3:11])[CH3:12]Participants
4
Procedure
The title compound was prepared according to the procedure for example 1-step 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 3-trifluoromethyl-benzylamine was used in place of 4-fluoro-benzylamine. Yield: 73%; mp: 237-239° C.; 1H NMR (300 MHz, DMSO-d6) δ 1.36 (s, 9H), 4.81-4.87 (m, 2H), 7.57 (s, 1H), 7.60-7.77 (m, 4H), 7.82 (brm, 1H); IR (KBr, cm-1): 3233m, 3059w, 2973w, 1793w, 1653s, 1571s, 1540s, 1471m, 1447m, 1354m, 1166m, 1127m; MS (CI) m/z (relative intensity): 327 (M+ +H, 80); Anal. Calcd. for C16H17 F3N2O2 : C, 58.89; H, 5.25; N, 8.58. Found: C, 58.99; H, 5.23; N, 8.47.
Sources & evidence
- ORD record
- ord-282d81664d9d4c5dac86997c0981cabb
- Source dataset
- uspto-grants-1998_05
- Patent number
- US05750574
Reaction notes
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