Isopropylamine → Methyl 4-[[[1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1h-pyrazol-5-yl]carbonyl]amino]-3-methyl-5-[[(1-methylethyl)amino]carbonyl]benzoate

HRID 1268894Notes

Reaction equation

[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]3[O:18][C:17](=[O:19])[C:16]4[CH:20]=[C:21](I)[CH:22]=[C:23]([CH3:24])[C:15]=4[N:14]=3)=[CH:11][C:10]([C:26]([F:29])([F:28])[F:27])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH:30]([NH2:33])([CH3:32])[CH3:31]>O1CCCC1>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([NH:14][C:15]3[C:16]([C:17]([NH:33][CH:30]([CH3:32])[CH3:31])=[O:19])=[CH:20][C:21]([C:17]([O:18][CH3:13])=[O:19])=[CH:22][C:23]=3[CH3:24])=[O:18])=[CH:11][C:10]([C:26]([F:28])([F:27])[F:29])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

The title compound of step B (3.07 g, 5.7 mmol) was dissolved in tetrahydrofuran (30 mL) and treated with isopropylamine (1.69 g, 28.7 mmol). The mixture was heated at 60° C. for 2 hours and concentrated to dryness under reduced pressure. The residue was subjected to chromatography on silica gel using ethyl acetate/hexanes (40:60) as eluent. Pooling appropriate fractions and evaporation of solvent provided the title compound of Step C (2.4 g): m.p.: 199–200° C. 1H NMR (CDCl3): δ 10.3 (NH), 8.42 (1H), 7.84 (1H), 7.61 (1H), 7.44 (2H), 7.42 (1H), 6.01 (1H), 4.21 (m, 1H), 2.13 (s, 3H), 1.2 (6H).

Workup

concentrationconcentrated to dryness under reduced pressure
customPooling appropriate fractions and evaporation of solvent

Sources & evidence

ORD record: ord-a661f3e6e500420ea563a3af671799e5
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199138B2

Reaction notes

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