Hydrochloric Acid → 4-(2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-indazol-3-amine

HRID 1909925Notes

Reaction equation

[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]3)[N:4]([CH3:27])[N:3]=1.Cl>CCO>[NH:16]1[C:17]2[C:13](=[CH:12][C:11]([C:9]3[CH:8]=[CH:7][CH:6]=[C:5]4[C:10]=3[C:2]([NH2:1])=[N:3][N:4]4[CH3:27])=[CH:19][CH:18]=2)[CH2:14][CH2:15]1

Participants

Conditions

Temperature: 75 °C

Procedure

To a stirred suspension of 1,1-dimethylethyl 5-(3-amino-1-methyl-1H-indazol-4-yl)-2,3-dihydro-1H-indole-1-carboxylate (1.70 g, 4.66 mmol) in 20 mL of EtOH was added 12 mL of 2N HCl. The mixture was heated at 75° C. for 90 min. LCMS showed conversion complete. The mixture was cooled, and concentrated in vacuo. The oily residue was diluted with 40 mL of water, and the pH was adjusted to ˜10 by adding 1N NaOH (pH paper). The milky mixture was extracted with 10° A MeOH in DCM (100 mL, then 2×25 mL). The combined organic was dried over Na2SO4, filtered, and concentrated in vacuo to give 4-(2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-indazol-3-amine as a brownish foamy solid (1.13 g). LC-MS (ES) m/z=265 [M+H]+.

Workup

temperatureThe mixture was cooled
concentrationconcentrated in vacuo
additionThe oily residue was diluted with 40 mL of water
additionby adding 1N NaOH (pH paper)
extractionThe milky mixture was extracted with 10° A MeOH in DCM (100 mL
dry with materialThe combined organic was dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-779ac28084634a5fb1ab05999f1487ae
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598156B2

Reaction notes

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