HCID 86680457, compound → HCID 86680459, compound

HRID 1184593Notes

Reaction equation

HRID 1184593 reaction equation
[CH2:1]=[C:2]([C:4]1[N:5]=[CH:6][C:7]([O:10][C@H:11]2[CH2:26][N:14]3[CH2:15][CH2:16][N:17](C(OC(C)(C)C)=O)[CH2:18][C@@H:13]3[CH2:12]2)=[N:8][CH:9]=1)[CH3:3]>Cl.O1CCOCC1>[CH2:1]=[C:2]([C:4]1[N:5]=[CH:6][C:7]([O:10][C@H:11]2[CH2:26][N:14]3[CH2:15][CH2:16][NH:17][CH2:18][C@@H:13]3[CH2:12]2)=[N:8][CH:9]=1)[CH3:3]

Participants

3

Reactant 1

HCID 86680457HCID 86680457, compound

Product 1

HCID 86680459HCID 86680459, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

The product from Example 152B (157 mg, 0.436 mmol) was dissolved in 2 mL of 4 M HCl-dioxane and stirred at room temperature for 30 minutes. The mixture was concentrated under a stream of nitrogen and the residue was purified by chromatography on a 12 g silica gel column, eluting with 2.5% methanol (containing 2 N ammonia) in dichloromethane for 3 minutes followed by a gradient to 10% methanol (2 N ammonia) in dichloromethane to afford the title compound as a colorless glass (102 mg, 90%). 1H NMR (300 MHz, CDCl3) δ ppm 8.24-8.20 (m, 1H), 8.15 (d, J=1.4 Hz, 1H), 5.80 (t, J=2.6 Hz, 1H), 5.43-5.32 (m, 1H), 5.22 (p, J=1.4 Hz, 1H), 3.77-3.68 (m, 1H), 3.12 (ddd, J=7.2, 5.3, 1.8 Hz, 1H), 3.03-2.93 (m, 2H), 2.84 (ddt, J=7.3, 5.8, 2.9 Hz, 1H), 2.55-2.44 (m, 1H), 2.37-2.21 (m, 4H), 2.20-2.15 (m, 3H), 2.00-1.83 (m, 2H).

Workup

  1. concentrationThe mixture was concentrated under a stream of nitrogen
  2. customthe residue was purified by chromatography on a 12 g silica gel column
  3. washeluting with 2.5% methanol (containing 2 N ammonia) in dichloromethane for 3 minutes

Sources & evidence

ORD record
ord-93f05aaa17b249219faa4a94130439cb
Source dataset
uspto-grants-2014_03
Patent number
US08669255B2

Reaction notes

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