Formic Acid → 6-Ethyl-2-formamido-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide

HRID 1483215

Reaction equation

HRID 1483215 reaction equation
[NH2:1][C:2]1[S:12][C:5]2[CH2:6][N:7]([CH2:10][CH3:11])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:13]([NH2:15])=[O:14].[CH:16](O)=[O:17]>O>[CH2:10]([N:7]1[CH2:8][CH2:9][C:4]2[C:3]([C:13]([NH2:15])=[O:14])=[C:2]([NH:1][CH:16]=[O:17])[S:12][C:5]=2[CH2:6]1)[CH3:11]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 6144392-Amino-6-ethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide

Product 1

HCID 1182701446-Ethyl-2-formamido-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamideYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of compound F4 (225 mg, 1.00 mmol) in formic acid (5 mL) and water (1 mL) was stirred overnight at room temperature. After that time, the reaction mixture was concentrated under reduced pressure. The residue was mixed with saturated aqueous sodium bicarbonate (50 mL) and extracted with methylene chloride (3×150 mL). The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel eluting with methanol/methylene chloride (15:85) to afford compound N1 as an off-white solid (208 mg, 82%): 1H NMR (300 MHz, DMSO-d6) δ 11.44 (s, 1H), 8.40 (s, 1H), 7.52 (bs, 1H), 7.03 (bs, 1H), 3.48 (s, 2H), 2.76 (d, J=4.8 Hz, 2H), 2.65 (d, J=4.8 Hz, 2H), 2.54-2.47 (m, 2H), 1.07 (t, J=7.0 Hz, 3H). MS (M+H) 254.

Workup

  1. concentrationAfter that time, the reaction mixture was concentrated under reduced pressure
  2. additionThe residue was mixed with saturated aqueous sodium bicarbonate (50 mL)
  3. extractionextracted with methylene chloride (3×150 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by flash column chromatography on silica gel eluting with methanol/methylene chloride (15:85)

Sources & evidence

ORD record
ord-9e51707642514ed18703b8cb94e681bc
Source dataset
uspto-grants-2016_08
Patent number
US09416141B2

Linked notes

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