Ammonium Chloride → HCID 59129468, compound

HRID 2038101Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[CH:17]=[C:18]5[C:22](=[CH:23][CH:24]=4)[N:21]([CH2:25][CH2:26][C:27]#[N:28])[CH:20]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:19]5)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[NH4+].[Cl-].[N-:35]=[N+:36]=[N-:37].[Na+]>CN(C=O)C>[N:28]1[NH:35][N:36]=[N:37][C:27]=1[CH2:26][CH2:25][N:21]1[C:22]2[C:18](=[CH:17][C:16]([NH:15][C:13]([C:10]3([C:8]4[CH:7]=[CH:6][C:5]5[O:1][CH2:2][O:3][C:4]=5[CH:9]=4)[CH2:12][CH2:11]3)=[O:14])=[CH:24][CH:23]=2)[CH:19]=[C:20]1[C:29]([CH3:32])([CH3:31])[CH3:30]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 1-(benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butyl-1-(2-cyano-ethyl)indolin-5-yl)cyclopropanecarboxamide (50 mg, 0.12 mmol) in anhydrous DMF (2.6 mL) was added NH4Cl (230 mg, 4.3 mmol) and NaN3(280 mg, 4.3 mmol). The reaction mixture was stirred for 30 min at 110° C. in the microwave, filtrated, and purified by preparative HPLC. The solid residue was dissolved in CDCl3(3 mL) and briefly (2 to 4 min) exposed to daylight, which initiated a color change (purple). After 2 h of stirring open to the atmosphere at room temperature, the solvent was removed and the residue was purified by preparative HPLC to give N-(1-(2-(2H-tetrazol-5-yl)ethyl)-2-tert-butyl-1H-indol-5-yl)-1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide. MS (ESI) m/e (M+H+) 473.0.

Workup

filtrationfiltrated
custompurified by preparative HPLC
dissolutionThe solid residue was dissolved in CDCl3(3 mL)
custombriefly (2 to 4 min)
stirringAfter 2 h of stirring open to the atmosphere at room temperature
customthe solvent was removed
customthe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-e5991d26902943e2a7e2df720bc35502
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575209B2

Reaction notes

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