p-Toluenesulfonic acid → Methyl 1-[(5-chloro-1-isobutyl-indazol-7-yl)methyl]-3-(methylamino)indazole-5-carboxylate

HRID 2203185Notes

Reaction equation

[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=2)[N:4]([CH2:15][C:16]2[CH:17]=[C:18]([Cl:29])[CH:19]=[C:20]3[C:24]=2[N:23]([CH2:25][CH:26]([CH3:28])[CH3:27])[N:22]=[CH:21]3)[N:3]=1.[C:30]1(C)C=CC(S(O)(=O)=O)=CC=1>COC(OC)OC>[Cl:29][C:18]1[CH:19]=[C:20]2[C:24](=[C:16]([CH2:15][N:4]3[C:5]4[C:10](=[CH:9][C:8]([C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=4)[C:2]([NH:1][CH3:30])=[N:3]3)[CH:17]=1)[N:23]([CH2:25][CH:26]([CH3:27])[CH3:28])[N:22]=[CH:21]2

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of compound 67 (0.054 g, 0.13 mmol), p-toluenesulphonic acid (0.003 g, 0.013 mmol), in trimethylorthoformate (3 mL) was heated at 100° C. in a closed vessel for 16 h. Then, the reaction was concentrated to dryness under vaccum. The residue was dissolved in tetrahydrofuran (4 mL), sodium borohydride was added (0.015 g, 0.395 mmol) and the resulting mixture was heated at 60° C. for 5 h.

Workup

concentrationThen, the reaction was concentrated to dryness under vaccum
dissolutionThe residue was dissolved in tetrahydrofuran (4 mL)
additionsodium borohydride was added (0.015 g, 0.395 mmol)

Sources & evidence

ORD record: ord-b4ccca167b04417eaa955f18a00243b6
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365569B2

Reaction notes

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