1-Benzyl 3-ethyl 4-fluoroisophthalate → 1-Benzyl 3-ethyl 4-(3-(butyl(3,4-dichlorobenzyl)carbamoyl)-4-chloro-5-methyl-1H-pyrazol-1-yl)isophthalate

HRID 528940Notes

Reaction equation

HRID 528940 reaction equation
F[C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][C:3]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].[CH2:23]([N:27]([CH2:37][C:38]1[CH:43]=[CH:42][C:41]([Cl:44])=[C:40]([Cl:45])[CH:39]=1)[C:28]([C:30]1[C:34]([Cl:35])=[C:33]([CH3:36])[NH:32][N:31]=1)=[O:29])[CH2:24][CH2:25][CH3:26]>>[CH2:23]([N:27]([CH2:37][C:38]1[CH:43]=[CH:42][C:41]([Cl:44])=[C:40]([Cl:45])[CH:39]=1)[C:28]([C:30]1[C:34]([Cl:35])=[C:33]([CH3:36])[N:32]([C:2]2[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:7])=[CH:4][C:3]=2[C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:31]=1)=[O:29])[CH2:24][CH2:25][CH3:26]

Participants

3

Reactant 2

HCID 710609931-Benzyl 3-ethyl 4-fluoroisophthalate2×HCID 71062158N-Butyl-4-chloro-N-(3,4-dichlorobenzyl)-5-methyl-1H-pyrazole-3-carboxamide2×

Product 1

HCID 710607101-Benzyl 3-ethyl 4-(3-(butyl(3,4-dichlorobenzyl)carbamoyl)-4-chloro-5-methyl-1H-pyrazol-1-yl)isophthalateYield 78,328.703%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 1E, 1-benzyl 3-ethyl 4-fluoroisophthalate (Intermediate 91B, 270 mg, 0.89 mmol) and N-butyl-4-chloro-N-(3,4-dichlorobenzyl)-5-methyl-1H-pyrazole-3-carboxamide (Intermediate 179B, 502 mg, 1.34 mmol) were converted to the title compound (458 g, 78%). 1H NMR (CDCl3, mixture of amide rotamers) δ 8.68 (dd, J=19.3, 1.9 Hz, 1H), 8.33 (dt, J=7.9, 2.0 Hz, 1H), 7.54-7.34 (m, 8H), 7.24-7.07 (m, 1H), 5.43 (d, J=3.1 Hz, 2H), 4.79-4.63 (m, 2H), 4.19 (q, J=7.3 Hz, 1H), 3.94 (q, J=7.2 Hz, 1H), 3.48-3.33 (m, 2H), 2.16 (d, J=6.6 Hz, 3H), 1.68-1.46 (m, 2H), 1.41-1.31 (m, 1H), 1.25-1.14 (m, 2.5H), 1.09 (t, J=7.2 Hz, 1.5H), 0.96-0.88 (m, 1.5H), 0.79 (t, J=7.4 Hz, 1.5H); MS(ESI+) m/z 656.0 (M+H)+.

Sources & evidence

ORD record
ord-14f9c5f5830b4ade9777f98aee32f3c6
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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