Triethylamine → HCID 11632543, compound

HRID 1991456Notes

Reaction equation

HRID 1991456 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:13])=[C:8]([OH:12])[C:9]=2[CH3:11])[S:4][C:3]=1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].CCN(CC)CC.[N:28]1([C:33](Cl)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]1>CC#N>[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:13])=[C:8]([O:12][C:33]([N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)=[O:34])[C:9]=2[CH3:11])[S:4][C:3]=1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 709371-Pyrrolidinecarbonyl chlorideHCID 59129736HCID 59129736, compound

Product 1

HCID 11632543HCID 11632543, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

tert-Butyl 3-amino-5-hydroxy-4,6-dimethyl-thieno[2,3-b]pyridine-2-carboxylate, prepared in example 1C, Step C, (40 mg, 0.14 mmol) in CH3CN (1 mL) was combined with Et3N (52 mg, 0.52 mmol) and pyrrolidine-1-carbonyl chloride (51 mg, 0.39 mmol) at room temperature. After stirring for 3 h, the mixture was evaporated under reduced pressure, water was added and extracted with ethyl acetate (3 mL), washed with water (3 mL×3), brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by preparative HPLC to provide tert-butyl 3-amino-4,6-dimethyl-5-(pyrrolidine-1-carbonyloxy)-thieno[2,3-b]pyridine-2-carboxylate (41 mg, 52%).

Workup

  1. customthe mixture was evaporated under reduced pressure, water
  2. additionwas added
  3. extractionextracted with ethyl acetate (3 mL)
  4. washwashed with water (3 mL×3), brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-89adc2f5b28a461599704ea5a56de172
Source dataset
uspto-grants-2010_01
Patent number
US07645881B2

Reaction notes

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