3-Aminopyridine → 5-(4-Morpholinylsulfonyl)-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

HRID 1623782Notes

Reaction equation

HRID 1623782 reaction equation
C(Cl)(=O)C(Cl)=O.[N:7]1([S:13]([C:16]2[CH:17]=[CH:18][C:19]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[C:20]([CH:24]=2)[C:21](O)=[O:22])(=[O:15])=[O:14])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]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>[N:7]1([S:13]([C:16]2[CH:17]=[CH:18][C:19]([O:25][CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[C:20]([CH:24]=2)[C:21]([NH:39][C:35]2[CH:34]=[N:33][CH:38]=[CH:37][CH:36]=2)=[O:22])(=[O:15])=[O:14])[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 100093-AminopyridineHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 454195635-(4-Morpholinylsulfonyl)-2-[(phenylmethyl)oxy]benzoic acid

Product 1

HCID 699364245-(4-Morpholinylsulfonyl)-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Conditions

Temperature
25 °C

Procedure

A solution of oxalyl chloride (0.06 ml, 0.66 mmol) in dichloromethane (5 ml) was added dropwise over 1 min to a stirred solution of 5-(4-morpholinylsulfonyl)-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 66; 250 mg, 0.66 mmol) in dichloromethane (5 ml) at 0° C. The reaction mixture was stirred at 25° C. for 0.5 h. The organic phase was evaporated in vacuo to give the crude acyl chloride as a yellow solid. A solution of this crude acyl chloride in dichloromethane (5 ml) was added dropwise over 5 min to a stirred solution of 3-pyridinamine (62.3 mg, 0.66 mmol) and diisopropylethylamine (0.12 ml, 0.66 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 and saturated brine (10 ml) two times, dried over sodium sulfate, and evaporated in vacuo to give the crude product as a orange oil.

Workup

  1. customThe organic phase was evaporated in vacuo
  2. customto give the crude acyl chloride as a yellow solid
  3. stirringThe reaction mixture was stirred at 25° C. for 1 h
  4. washThe organic phase was washed with water (25 ml) three times and saturated brine (10 ml) two times
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-9f1ccee39964431e97f7fb84752e2bf5
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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