HCID 58423402, compound → HCID 58423128, compound

HRID 1398010Notes

Reaction equation

HRID 1398010 reaction equation
[Si]([O:8][CH2:9][CH2:10][NH:11][CH:12]1[CH2:16][CH2:15][N:14]([C:17]2[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[CH:27][C:18]=2/[CH:19]=[C:20]2/[C:21](=[O:26])[NH:22][C:23](=[O:25])[S:24]/2)[CH2:13]1)(C(C)(C)C)(C)C>Cl.CO>[OH:8][CH2:9][CH2:10][NH:11][CH:12]1[CH2:16][CH2:15][N:14]([C:17]2[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[CH:27][C:18]=2/[CH:19]=[C:20]2/[C:21](=[O:26])[NH:22][C:23](=[O:25])[S:24]/2)[CH2:13]1

Participants

4

Reactant 1

HCID 58423402HCID 58423402, compound

Product 1

HCID 58423128HCID 58423128, compoundYield 48.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of (Z)-5-(2-(3-(2-(tert-butyldimethylsilyloxy)ethylamino)pyrrolidin-1-yl)-4,5-dimethoxybenzylidene)thiazolidine-2,4-dione (Method 77) (120 mg, 0.24 mmol) in 5 mL of 1.25 M HCl in methanol was stirred at room temperature for 30 min. The mixture was then conc. in vacuo to afford the product which was purified via reverse phase HPLC (acetonitrile:water: 0.1% NH4OAc=5% to 55%) to yield the title compound as a yellow solid (45.0 mg, 48.4%). 1H NMR (300 MHz, DMSO-D6) δ ppm 7.40 (s, 1 H) 7.07 (s, 1 H) 6.57 (s, 1 H) 3.78 (s, 3 H) 3.70 (s, 3 H) 3.45 (m, 2 H) 3.27-3.15 (m, 4 H) 2.92 (m, 1 H) 2.59 (m, 2 H) 2.08 (m, 1 H) 1.66 (m, 1 H); m/z 394.

Workup

  1. customconc. in vacuo to afford the product which
  2. customwas purified via reverse phase HPLC (acetonitrile:water: 0.1% NH4OAc=5% to 55%)

Sources & evidence

ORD record
ord-bc401feccc9442cea2cb5dbf0c1ca0ee
Source dataset
uspto-grants-2014_12
Patent number
US08901307B2

Reaction notes

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