1-Benzyl 3-ethyl 4-fluoroisophthalate → 1-Benzyl 3-ethyl 4-(4-chloro-3-(dipropylamino)-5-methyl-1H-pyrazol-1-yl)isophthalate
Reaction equation
[Cl:1][C:2]1[C:3]([N:8]([CH2:12][CH2:13][CH3:14])[CH2:9][CH2:10][CH3:11])=[N:4][NH:5][C:6]=1[CH3:7].F[C:16]1[CH:31]=[CH:30][C:19]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])=[CH:18][C:17]=1[C:32]([O:34][CH2:35][CH3:36])=[O:33]>>[Cl:1][C:2]1[C:3]([N:8]([CH2:9][CH2:10][CH3:11])[CH2:12][CH2:13][CH3:14])=[N:4][N:5]([C:16]2[CH:31]=[CH:30][C:19]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])=[CH:18][C:17]=2[C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:6]=1[CH3:7]Participants
3
Procedure
Following a procedure analogous to that for the synthesis of Intermediate 1E, 4-chloro-5-methyl-N,N-dipropyl-1H-pyrazol-3-amine (290 mg, 1.34 mmol) and 1-benzyl 3-ethyl 4-fluoroisophthalate (Intermediate 91B, 447 mg, 1.48 mmol) were converted to the title compound (315 mg, 47%). 1H NMR (CDCl3) δ 8.55 (d, J=2.0 Hz, 1H), 8.27 (dd, J=8.3, 2.1 Hz, 1H), 7.54-7.32 (m, 6H), 5.43 (s, 2H), 4.20 (q, J=7.0 Hz, 2H), 3.32-3.17 (m, 4H), 2.17 (s, 3H), 1.69-1.54 (m, 6H), 1.21 (t, J=7.2 Hz, 3H), 0.92 (t, J=7.4 Hz, 6H); MS(ESI+) m/z 498.2 (M+H)+.
Sources & evidence
- ORD record
- ord-dc426703155140fdb9a6f34c88a86df4
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346795B2
Reaction notes
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