HCID 70140565, compound → HCID 70080987, compound

HRID 1938762Notes

Reaction equation

HRID 1938762 reaction equation
[NH2:1][N:2]=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([NH:12][C:13]2[CH:14]=[CH:15][C:16]3[NH:22][CH:21]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[C:20](=[O:28])[N:19]([CH2:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH2:18][C:17]=3[CH:37]=2)=[O:11])=[CH:6][CH:5]=1>CS(C)=O>[NH2:1][N:2]=[CH:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]([NH:12][C:13]2[CH:14]=[CH:15][C:16]3[N:22]=[C:21]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[C:20](=[O:28])[N:19]([CH2:29][CH2:30][C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH2:18][C:17]=3[CH:37]=2)=[O:11])=[CH:8][CH:9]=1

Participants

3

Reactant 1

HCID 70140565HCID 70140565, compound

Product 1

HCID 70080987HCID 70080987, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The compound of Example 8 was dissolved in DMSO and air was bubbled through the solution overnight. The mixture was quenched with ice water and filtered to give a crude solid which was flash chromatographed (octadecylsilane silica gel, 60% CH3CN/H2O/0.1% TFA) to yield the title compound. MS(ES) 498 [M+H]+, 496 [M-H]- ; Anal. (C28H27N5O4.1.85 TFA.0.25 H2O) calcd: C, 53.40; H, 4.15; N, 9.82. found: C, 53.52; H, 4.42; N, 9.72.

Workup

  1. customair was bubbled through the solution overnight
  2. customThe mixture was quenched with ice water
  3. filtrationfiltered
  4. customto give a crude solid which
  5. customchromatographed (octadecylsilane silica gel, 60% CH3CN/H2O/0.1% TFA)

Sources & evidence

ORD record
ord-0cc82490c2044426adc21d7280876555
Source dataset
uspto-grants-1997_12
Patent number
US05693636

Reaction notes

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