Potassium Bromide → HCID 18922793, 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:27])([F:26])[O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1.[K+].[Br-]>>[C:9]([NH:8][C:7]1[C:6](=[O:13])[C:5](=[O:14])[C:4]=1[NH:23][CH2:22][C:21]1[CH:24]=[CH:25][C:18]([O:17][C:16]([F:15])([F:26])[F:27])=[CH:19][CH:20]=1)([CH3:10])([CH3:11])[CH3:12]Participants
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 4-trifluoromethoxy-benzylamine was used in place of 4-fluoro-benzylamine. Yield: 66%; mp: 292°-294° C.; 1H NMR (300 MHz, DMSO-d6): δ1.36 (m, 9H), 4.73-4.79 (m 2H), 7.39 (d, J=8.0 Hz, 2H), 7.76 (d, J=8.2 Hz, 2H), 7.81 (brs, 1H), one N--H proton not seen; IR (KBr, cm-1): 3293s, 3242s, 3061w, 2980m, 1794m, 1655s, 1569s, 1542s, 1472s, 1447s, 1280-1160brs; MS (ES) m/z (relative intensity): 365 (M+ +Na, 100), 343 (M+ +H, 75); Anal. Calcd. for C16H17 F3N2O3 : C, 56.14; H, 5.01; N, 8.18. Found: C, 56.28; H, 5.05; N, 7.97.
Sources & evidence
- ORD record
- ord-3d60a6bfd2c1496a955363f3d84aafd0
- Source dataset
- uspto-grants-1998_05
- Patent number
- US05750574
Reaction notes
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