HCID 20400411, compound → HCID 118108306, compound

HRID 2174520Notes

Reaction equation

HRID 2174520 reaction equation
[C:1]([NH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([CH3:18])=[CH:12]2)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:19]([O:21]C1C=C2C(=CC=1)NC(C)=C2C=O)C>>[C:1]([NH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([CH3:18])=[C:12]2[CH:19]=[O:21])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

3

Reactant 2

HCID 20400411HCID 20400411, compoundHCID 85785374HCID 85785374, compound

Product 1

HCID 118108306HCID 118108306, compoundYield 36%

Procedure

This compound was prepared from 412 (615 mg, 2.24 mmol) in a manner similar to that for 409a except for after the drop-wise addition of substituted indole, the solution was stirred for 4 h to provide an orange precipitate. The precipitate was further purified by chromatography (isocratic 5% MeOH/DCM) to yield a white solid (250 mg, 36%): mp 201-203° C. TLC Rf 0.33 (75% EtOAc/hexanes). 1H NMR (600 MHz, d6-DMSO) δ 9.70 (s, 1H), 8.08 (s, 1H), 7.26-7.24 (m, 2H), 2.69 (s, 3H), 1.52 (s, 9H). 13C NMR (150 MHz, d6-DMSO) δ 184.4, 153.4, 149.4, 134.5, 131.6, 125.9, 115.6, 113.9, 111.4, 110.3, 79.0, 28.5, 11.7. Elemental analysis calculated for C15H18N2O3.0.125H2O: C, 65.14; H, 6.65; N, 10.13. Found: C, 64.82; H, 6.81; N, 10.14. HRMS ESI calculated for C15H18N2O3 (M+H)+ 275.1390; (M+Na)+ 297.1210. Found (M+H)+ 275.1393; (M+Na)+ 297.1210.

Workup

  1. customto provide an orange precipitate
  2. customThe precipitate was further purified by chromatography (isocratic 5% MeOH/DCM)

Sources & evidence

ORD record
ord-95cca6ef90464735a46e5f2428b1e628
Source dataset
uspto-grants-2015_06
Patent number
US09061994B1

Reaction notes

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