PNU-159682 → HCID 59184910, compound

HRID 1943320Notes

Reaction equation

HRID 1943320 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][S:9][CH2:10][CH2:11][C:12]([NH:14][NH2:15])=[O:13].[OH:16][C:17]1[C:34]2[CH2:33][C@@:32]([OH:39])([C:35](=O)[CH2:36][OH:37])[CH2:31][C@H:30]([O:40][C@@H:41]3[O:55][C@@H:54]([CH3:56])[C@H:44]4[O:45][C@H:46]5[N:51]([C@H:43]4[CH2:42]3)[CH2:50][CH2:49][O:48][C@@H:47]5[O:52][CH3:53])[C:29]=2[C:28]([OH:57])=[C:27]2[C:18]=1[C:19](=[O:61])[C:20]1[CH:21]=[CH:22][CH:23]=[C:24]([O:59][CH3:60])[C:25]=1[C:26]2=[O:58]>CO>[OH:37][CH2:36]/[C:35](=[N:15]\[NH:14][C:12](=[O:13])[CH2:11][CH2:10][S:9][S:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=1)/[C@@:32]1([OH:39])[CH2:31][C@H:30]([O:40][C@@H:41]2[O:55][C@@H:54]([CH3:56])[C@H:44]3[O:45][C@H:46]4[N:51]([C@H:43]3[CH2:42]2)[CH2:50][CH2:49][O:48][C@@H:47]4[O:52][CH3:53])[C:29]2[C:34](=[C:17]([OH:16])[C:18]3[C:19](=[O:61])[C:20]4[C:25]([C:26](=[O:58])[C:27]=3[C:28]=2[OH:57])=[C:24]([O:59][CH3:60])[CH:23]=[CH:22][CH:21]=4)[CH2:33]1

Participants

4

Reactant 2

HCID 9874188PNU-159682HCID 87276894178558-20-8

Product 1

HCID 59184910HCID 59184910, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(2-pyridyldithio)propionic acid hydrazide HCl (41.5 mg, 0.156 mmol) in anhydrous methanol (5 ml) was added to (8S,10S)-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-10-{[(1S,3R,4aS,9S,9aR,10aS)-9-methoxy-1-methyloctahydro-1H-pyrano[4′,3′:4,5][1,3]oxazolo[2,3-c][1,4]oxazin-3-yl]oxy}-7,8,9,10-tetrahydrotetracene-5,12-dione [PNU-159682, compound IIA, prepared as reported in WO 9802446] (50 mg, 0.078 mmol). The solution was stirred in the dark at room temperature for 20 hours. The course of the reaction was followed by reverse-phase HPLC-MS. After this period the solvent was evaporated and the residue was purified by flash column chromatography (MeOH:CH2Cl2=0.2:9.8) on silica gel (230-400 mesh), affording 18 mg (yield 27%) of 53. MS (ESI): 853 [M+H]+. Retention time=5.52 min (method 2).

Workup

  1. customAfter this period the solvent was evaporated
  2. customthe residue was purified by flash column chromatography (MeOH:CH2Cl2=0.2:9.8) on silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-be02fe4e192d42c5919d9f2800dd0a6f
Source dataset
uspto-grants-2013_03
Patent number
US08389697B2

Reaction notes

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