Methylamine → 2-(4-bromophenyl)-5-cyclopropyl-N-methyl-6-nitro-2H-indazole-3-carboxamide

HRID 1037525Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17](O)=[O:18])=[C:15]3[C:10]([CH:11]=[C:12]([N+:23]([O-:25])=[O:24])[C:13]([CH:20]4[CH2:22][CH2:21]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1.[CH3:26][NH2:27].O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]([NH:27][CH3:26])=[O:18])=[C:15]3[C:10]([CH:11]=[C:12]([N+:23]([O-:25])=[O:24])[C:13]([CH:20]4[CH2:22][CH2:21]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of compound (vii) (2.2 g, 5.5 mmol) in pyridine (45 mL) was added methyl amine (8.2 mL, 2 M solution in THF, 16 mmol). The reaction mixture was cooled to 0° C. and POCl3 (2.88 g, 19 mmol) was added dropwise at the same temperature. After 1 h TLC and LCMS showed the absence of SM and formation of product. The reaction mixture was quenched in ice water and the precipitate was filtered and crystallized from MeOH to give 2-(4-bromophenyl)-5-cyclopropyl-N-methyl-6-nitro-2H-indazole-3-carboxamide (viii) (1.25 g, 55%). ESI-MS m/z calculated for [M+H]+: 415.04/417.04; found: 415.15/417.15.

Workup

customThe reaction mixture was quenched in ice water
filtrationthe precipitate was filtered
customcrystallized from MeOH

Sources & evidence

ORD record: ord-367c7fe9133542a596cac735c023d700
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546389B2

Reaction notes

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