Hydrochloric Acid → Methyl 7-{3-[(3-methyl-2-furoyl)amino]phenoxy}thieno[3,2-b]pyridine-2-carboxylate

HRID 525828Notes

Reaction equation

HRID 525828 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([OH:9])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:43][C:44]1[CH:45]=[C:46]([CH:61]=[CH:62][CH:63]=1)[O:47][C:48]1[CH:53]=[CH:52][N:51]=[C:50]2[CH:54]=[C:55]([C:57]([O:59][CH3:60])=[O:58])[S:56][C:49]=12.Cl>CN(C=O)C.O>[CH3:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([NH:43][C:44]1[CH:45]=[C:46]([CH:61]=[CH:62][CH:63]=1)[O:47][C:48]1[CH:53]=[CH:52][N:51]=[C:50]2[CH:54]=[C:55]([C:57]([O:59][CH3:60])=[O:58])[S:56][C:49]=12)=[O:9]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 781273-Methyl-2-furoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 117690318Methyl 7-(3-aminophenoxy)thieno[3,2-b]pyridine-2-carboxylate

Product 1

HCID 86290322Methyl 7-{3-[(3-methyl-2-furoyl)amino]phenoxy}thieno[3,2-b]pyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-methyl-2-furoic acid (166 mg, 1.32 mmol) in anhydrous DMF (10 ml) were added HATU (552 mg, 1.45 mmol) and DIPEA (341 mg, 2.64 mmol). The mixture was stirred at room temperature for 10 minutes, and 330 mg of crude methyl 7-(3-aminophenoxy)thieno[3,2-b]pyridine-2-carboxylate from step 1 was added. The mixture was then heated at 65° C. for 2 hours, cooled to room temperature, and poured into 100 ml of water. 2M HCl was added until pH=4. The precipitates were filtered, washed with water and dried to give the crude, which was purified by silica gel chromatography eluting with 2˜3% of MeOH in chloroform to afford methyl 7-{3-[(3-methyl-2-furoyl)amino]phenoxy}thieno[3,2-b]pyridine-2-carboxylate as off-white solid. Yield: 230 mg, 26% for 2 steps.

Workup

  1. temperatureThe mixture was then heated at 65° C. for 2 hours
  2. temperaturecooled to room temperature
  3. filtrationThe precipitates were filtered
  4. washwashed with water
  5. customdried
  6. customto give the crude, which
  7. customwas purified by silica gel chromatography
  8. washeluting with 2˜3% of MeOH in chloroform

Sources & evidence

ORD record
ord-0361bff6230348d79ec3b81b259f58ea
Source dataset
uspto-grants-2016_05
Patent number
US09340555B2

Reaction notes

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