Pyridine → HCID 178431221, compound

HRID 1420746Notes

Reaction equation

HRID 1420746 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([C:18]2[CH:31]=[CH:30][C:21]3[O:22][C:23]([CH3:29])([CH3:28])[C@@:24]4([CH3:27])[O:26][C@H:25]4[C:20]=3[CH:19]=2)(=[O:17])=[O:16])=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[OH:32][C:33]1[N:34]=[N:35][C:36]([OH:39])=[CH:37][CH:38]=1.N1C=CC=CC=1>C(O)C>[OH:26][C@:24]1([CH3:27])[C:23]([CH3:28])([CH3:29])[O:22][C:21]2[CH:30]=[CH:31][C:18]([S:15]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=3)(=[O:17])=[O:16])=[CH:19][C:20]=2[C@H:25]1[O:39][C:36]1[N:35]=[N:34][C:33]([OH:32])=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 57308558HCID 57308558, compoundHCID 178516298pyridazine-3,6-diol

Product 1

HCID 178431221HCID 178431221, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(3S,4S)-6-(4-tert-Butyldimethylsilyloxyphenyl)sulphonyl-3,4-dihydro-3,4-epoxy-2,2,3-trimethyl-2H-benzo[b]pyran (0.35 g) (see Preparation 14) and 3,6-dihydroxypyridazine (0.273 g) were suspended in absolute ethanol (3 ml), dry pyridine (0.065 ml) was added and the mixture was heated under reflux for 4 days. The solvent was then removed under reduced pressure and the residue chromatographed on silica with 1:99 methanol:ethyl acetate as the eluent to yield (3S,4R)-3,4-dihydro-3-hydroxy-6-(4-hydroxyphenyl)sulphonyl-4-(3-hydroxypyridazin-6-yl)oxy-2,2,3-trimethyl-2H-benzo[b]pyran (0.155 g) as a white solid, m.p. >200° C. Found: C,57.54; H,5.35; N,5.57. C22H22N2O7S, 0.20 ethyl acetate requires C,57.50; H,4.99; N,5.88%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 days
  3. customThe solvent was then removed under reduced pressure
  4. customthe residue chromatographed on silica with 1:99 methanol

Sources & evidence

ORD record
ord-414c592e359744b8a2008c5343413339
Source dataset
uspto-grants-2000_06
Patent number
US06071938

Reaction notes

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