HCID 178514727, compound → HCID 178514729, compound

HRID 1168227Notes

Reaction equation

HRID 1168227 reaction equation
[O:1]=[C:2]1[NH:10][C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[C:3]1=[CH:11][NH:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1>O>[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]1=[CH:11][NH:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

3

Reactant 1

HCID 178514727HCID 178514727, compound

Product 1

HCID 178514729HCID 178514729, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Inorganics were removed by filtration through a short silica gel column, eluting with DMF. The resulting solution was diluted with an equal volume of ice water, and the suspension was refrigerated overnight. The solid was isolated by filtration and dried to give 36 mg (21%) of the title compound as a yellow solid: 1H NMR (400 MHz, DMSO-d6) (4:1 ratio of Z:E isomers): δ (Z) 11.07 (s, 1H), 10.76 (d, J=12.4 Hz, 1H), 8.67 (d, J=12.5 Hz, 1H), 7.92 (d, J=5.1 Hz, 1H), 7.84 (d, J=7.3 Hz, 1H), 7.77 (d, J=8.7 Hz, 2H), 7.55 (d, J=8.6 Hz, 2H), 7.25 (s, 2H), 6.93 (dd, J=7.3, 5.1 Hz, 1H); (E) 10.79 (s, 1H), 9.70 (d, J=13.4 Hz, 1H), 8.23 (d, J=7.3 Hz, 1H). ESI−MS m/z 315 (M−H). Anal. Calcd. for C14H12N4O3S. 0.5 H2O: C, 51.68; H, 4.03; N, 17.03. Found: C, 51.75; H, 3.95; N, 17.26.

Workup

  1. customInorganics were removed by filtration through a short silica gel column
  2. washeluting with DMF
  3. additionThe resulting solution was diluted with an equal volume of ice water
  4. customThe solid was isolated by filtration
  5. customdried
  6. customto give 36 mg (21%) of the title compound as a yellow solid

Sources & evidence

ORD record
ord-a91685a724184dd7bb6c8df3860fd363
Source dataset
uspto-grants-2003_09
Patent number
US06624171B1

Reaction notes

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