HCID 24780398, compound → HCID 66884731, compound

HRID 2232958Notes

Reaction equation

HRID 2232958 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][C:9](=[O:11])[N:8]([CH:12]3[CH:16]([O:17]C(=O)C)[CH2:15][CH:14]([CH2:21][O:22][C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])[O:13]3)[C:6]=2[N:7]=1>CO>[CH:26]([O:25][C:23](=[O:24])[O:22][CH2:21][CH:14]1[CH2:15][CH:16]([OH:17])[CH:12]([N:8]2[C:6]3[N:7]=[C:2]([NH2:1])[N:3]=[CH:4][C:5]=3[S:10][C:9]2=[O:11])[O:13]1)([CH3:28])[CH3:27]

Participants

3

Reactant 1

HCID 24780398HCID 24780398, compound

Product 1

HCID 66884731HCID 66884731, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 4 (0.50 g, 1.21 mmol) was dissolved in MeOH (5.0 mL) and TEA (0.51 mL, 3.63 mmol) was added. The solution was stirred at rt for 48 hr and warmed to 35° C. from 48 to 72 hr. The reaction was removed from heat, concentrated in vacuo, then submitted to flash chromatography (0-100% EtOAc-DCM) yielding 0.298 g (66%) of 5 as a white powder: 1H NMR (400 MHz, DMSO-d6): 8.33 (1H, s), 6.85 (2H, bs), 5.85 (1H, d, J=2.3 Hz), 5.52 (1H, d, J=4.1 Hz), 4.79-4.83 (1H, m), 4.71 (1H, septet, J=6.2 Hz), 4.35-4.41 (1H, m), 4.23 (1H, dd, J1=3.8 Hz, J2=11.9 Hz), 4.06 (1H, dd, J1=8.0 Hz, J2=11.9 Hz), 2.40-2.47 (1H, m), 1.86-1.91 (1H, m), 1.20 (3H, d, J=1.4 Hz), 1.19 (3H, d, J=1.4 Hz); [M+H]+ at m/z 370.9. Analysis calc'd for C14H18N4O6S: C, 45.40; H, 4.90; N, 15.13; S, 8.66. Found: C, 45.07; H, 4.84; N, 14.70; S, 8.51.

Workup

  1. temperaturewarmed to 35° C. from 48 to 72 hr
  2. customThe reaction was removed
  3. temperaturefrom heat
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fc8cac768fd94f728c80a73bf83b197c
Source dataset
uspto-grants-2010_05
Patent number
US07709448B2

Reaction notes

Loading…