Sodium Bicarbonate → HCID 178489102, compound

HRID 2409535Notes

Reaction equation

HRID 2409535 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[S:15][C:14]3=[N:16][C:17]([CH3:27])=[C:18]([C:19]4[CH:20]=[N:21][C:22]([O:25]C)=[CH:23][CH:24]=4)[N:13]3[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C([O-])(O)=O.[Na+]>Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[S:15][C:14]3=[N:16][C:17]([CH3:27])=[C:18]([C:19]4[CH:24]=[CH:23][C:22]([OH:25])=[N:21][CH:20]=4)[N:13]3[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 46941036HCID 46941036, compound

Product 1

HCID 178489102HCID 178489102, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2-(3,4-dimethoxy-phenyl)-5-(6-methoxy-pyridin-3-yl)-6-methyl-imidazo[2,1-b][1,3,4]thiadiazole (0.028 g, 0.073 mmol, 1 eq) in 25% HCl (0.75 mL) was subjected to microwave irradiation (95° C., 2 h, 200 W). The reaction mixture was cooled to RT, neutralized with NaHCO3 (sat. sol) and extracted with EtOAc and subsequently with CH2Cl2/MeOH (9:1). The organic phase was dried (MgSO4), filtered and concentrated. The crude (0.007 g) was purified by preparative HPLC (RP-C18, ACN/water) affording the desired product (yellowish solid, 0.005 g, 19%). HPLC-MS: (5-100% B in 8 min, 0.8 mL/min, 50° C.): tR=3.94 min, [M+H]+ m/z 369.1; 1H NMR (300 MHz, CDCl3) δ/ppm 12.94 (s, 2H), 7.82 (dd, J=9.5, 2.5, 1H), 7.72 (d, J=2.2, 1H), 7.34 (dd, J=8.3, 2.0, 1H), 7.30 (d, J=2.0, 1H), 6.88 (d, J=8.4, 1H), 6.69 (d, J=9.5, 1H), 3.92 (s, 3H), 3.89 (s, 3H), 2.40 (s, 3H).

Workup

  1. extractionextracted with EtOAc and subsequently with CH2Cl2/MeOH (9:1)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude (0.007 g) was purified by preparative HPLC (RP-C18, ACN/water)

Sources & evidence

ORD record
ord-07f40e7b133f4e0994725e0768d9ea4f
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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