N-methyl-2-pyrrolidone → HCID 67265589, compound

HRID 1685744Notes

Reaction equation

HRID 1685744 reaction equation
[CH:1]([C:3]1[S:7][C:6]([C:8]2[N:9]=[N:10][O:11][CH:12]=2)=[CH:5][CH:4]=1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C[N:28]1C(=O)CCC1>C(Cl)Cl>[NH2:28][CH2:1][C:3]1[S:7][C:6]([C:8]2[N:9]=[N:10][O:11][CH:12]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 5049666Sodium triacetoxyborohydride3×HCID 86646448HCID 86646448, compound

Product 1

HCID 67265589HCID 67265589, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the 5-formyl-thiophen-2-yl-oxadiazol derivative (1 eq., usual scale 0.02-0.25 mmol) and the appropriate amine (2-40 eq.) in DCM (24 mL/mmol) and NMP (6 mL/mmol), sodium triacetoxy borohydride (NaBH(OAc)3) (3 eq.) is added. The mixture is stirred for 2 h before another portion of NaBH(OAc)3 (3 eq.) is added. Stirring of the suspension is continued for another 2 h and a third portion of NaBH(OAc)3 (3 eq.) is added. The mixture is stirred for 16 h before the DCM is evaporated. The remaining residue is diluted with water (4 mL/mmol) and formic acid (4 mL/mmol) and the resulting solution is separated by prep. HPLC (XBridge Prep C18, 19×50 mm, 5 μm, 10% to 95% acetonitrile in water containing 0.5% formic acid) to give the desired 5-aminomethyl-thiophen-2-yl-oxadiazol derivative as a colourless to pale yellow resin.

Workup

  1. additionis added
  2. customis evaporated
  3. additionThe remaining residue is diluted with water (4 mL/mmol) and formic acid (4 mL/mmol)
  4. customthe resulting solution is separated by prep

Sources & evidence

ORD record
ord-975467b08d734567b9988ea5de5ce512
Source dataset
uspto-grants-2012_04
Patent number
US08148410B2

Reaction notes

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