HCID 136343326, compound → HCID 136337756, compound

HRID 2252244Notes

Reaction equation

HRID 2252244 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:27](=[CH:28][C:29]=1[O:30][CH3:31])[C:7]1[N:8](COCC[Si](C)(C)C)[N:9]=[C:10]([C:11]3[CH:12]=[CH:13][C:14]([C:17]#[N:18])=[N:15][CH:16]=3)[C:6]=1[C:5]2([CH3:33])[CH3:32]>Cl.CCO>[OH:1][C:2]1[CH:3]=[C:4]2[C:27](=[CH:28][C:29]=1[O:30][CH3:31])[C:7]1[NH:8][N:9]=[C:10]([C:11]3[CH:12]=[CH:13][C:14]([C:17]#[N:18])=[N:15][CH:16]=3)[C:6]=1[C:5]2([CH3:33])[CH3:32]

Participants

4

Reactant 1

HCID 136343326HCID 136343326, compound

Product 1

HCID 136337756HCID 136337756, compoundYield 24.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

A mixture of Example 134D (23.0 mg, 0.0497 mmol) and HCl (concentrated, 2 drops) in EtOH (2 mL) was stirred at 75° C. for 1.5 hours. The solvent was evaporated and the residue was purified using reversed-phase HPLC to give the desired product (4.0 mg) as TFA salt. MS (ESI) m/z: 333.0 (M+H)+; 1H NMR (300 MHz, CD3OD) δ ppm 1.56 (s, 6H) 3.93 (s, 3H) 6.94 (s, 1H) 7.20 (s, 1H) 7.99 (d, J=8.14 Hz, 1H) 8.32 (dd, J=8.14, 2.37 Hz, 1H) 9.11 (d, J=2.37 Hz, 1H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified

Sources & evidence

ORD record
ord-ff4219705fbd4d00b1cf59d5c6c84540
Source dataset
uspto-grants-2008_01
Patent number
US07320986B2

Reaction notes

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