3-Aminopyridine → 2-[(Phenylmethyl)oxy]-5-(1-piperidinylsulfonyl)-N-3-pyridinylbenzamide

HRID 1623783Notes

Reaction equation

HRID 1623783 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]1([CH2:13][O:14][C:15]2[CH:23]=[CH:22][C:21]([S:24]([N:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)(=[O:26])=[O:25])=[CH:20][C:16]=2[C:17]([OH:19])=O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N:33]1[CH:38]=[CH:37][CH:36]=[C:35]([NH2:39])[CH:34]=1.C(N(C(C)C)CC)(C)C>ClCCl>[C:7]1([CH2:13][O:14][C:15]2[CH:23]=[CH:22][C:21]([S:24]([N:27]3[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]3)(=[O:25])=[O:26])=[CH:20][C:16]=2[C:17]([NH:39][C:35]2[CH:34]=[N:33][CH:38]=[CH:37][CH:36]=2)=[O:19])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 100093-AminopyridineHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 671074732-[(Phenylmethyl)oxy]-5-(1-piperidinylsulfonyl)benzoic acid

Product 1

HCID 699362452-[(Phenylmethyl)oxy]-5-(1-piperidinylsulfonyl)-N-3-pyridinylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Conditions

Temperature
25 °C

Procedure

Oxalyl chloride (0.05 ml, 0.59 mmol) in dichloromethane (5 ml) was added dropwise over 1 min to a stirred solution of 2-[(phenylmethyl)oxy]-5-(1-piperidinylsulfonyl)benzoic acid (may be prepared as described in Description 69; 220 mg, 0.59 mmol) in dichloromethane (5 ml) at 0° C. The reaction mixture was stirred at 25° C. for 0.5 h, and then concentrated under reduced pressure to give crude acyl chloride. A solution of this crude acyl chloride in dichloromethane (5 ml) was added dropwise over 5 min to a stirred solution of 3-pyridinamine (55.1 mg, 0.59 mmol) and diisopropylethylamine (0.10 ml, 0.59 mmol) in dichloromethane (20 ml) under nitrogen at 0° C. The reaction mixture was stirred at 25° C. for 1 h. The organic phase was washed with water (25 ml) three times, saturated brine (10 ml) two times, dried over sodium sulfate, and evaporated in vacuo to give crude product as a orange oil. The product was crystallized from methanol to yield the title compound as a white solid. 125 mg.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto give crude acyl chloride
  3. stirringThe reaction mixture was stirred at 25° C. for 1 h
  4. washThe organic phase was washed with water (25 ml) three times, saturated brine (10 ml) two times
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customto give crude product as a orange oil
  8. customThe product was crystallized from methanol

Sources & evidence

ORD record
ord-61a25bb58365427781a508b6048be550
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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