Formate → HCID 178520651, compound

HRID 1695232Notes

Reaction equation

HRID 1695232 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:22]2[CH:23]=[C:24]([NH2:27])[NH:25][N:26]=2)=[CH:14]1.C([O-])=O>ClCCCl>[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:22]2[CH:23]=[C:24]([NH:27][C:10](=[O:12])[CH2:9][CH2:8][CH2:7][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[NH:25][N:26]=2)=[CH:14]1

Participants

5

Reactant 3

HCID 283FormateHCID 20794Butyric acid, 4-piperidino-HCID 178507318HCID 178507318, compound

Product 1

HCID 178520651HCID 178520651, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a suspension of 4-piperidin-1-yl-butyric acid (621.0 mg, 3.0 mmol, 1.5 eq) in 1,2-dichloroethane (6 mL), N,N′-carbonyldiimidazole (453.0 mg, 2.8 mmol, 1.4 eq) was added and the mixture was stirred at room temperature for 1 hour. 5-(1H-indol-3-yl)-2H-pyrazol-3-ylamine (400.0 mg, 2.0 mmol, 1.0 eq) in 1,2-dichloroethane (6 mL) was added; the reaction was stirred at room temperature for 2 days, then 1 day at 70° C., to allow complete migration of the acyl group from the ring nitrogen to the exocyclic nitrogen. The reaction then was allowed to cool down to room temperature and the mixture was washed with saturated Na2CO3 and evaporated under reduced pressure; the crude was purified by preparative HPLC to give 320.0 mg (yield: 41%) of the title compound as formate salt.

Workup

  1. additionwas added
  2. stirringthe reaction was stirred at room temperature for 2 days
  3. custom1 day
  4. customat 70° C.
  5. customThe reaction
  6. temperatureto cool down to room temperature
  7. washthe mixture was washed with saturated Na2CO3
  8. customevaporated under reduced pressure
  9. customthe crude was purified by preparative HPLC

Sources & evidence

ORD record
ord-b81084ead30742eb84fa98e4418c991d
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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