Pyridine → HCID 86591406, compound

HRID 2220155Notes

Reaction equation

HRID 2220155 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][NH2:21])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[Cl:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1.CN(C1C=CC=CN=1)C.C(Cl)(=O)C1C=CC=CC=1>C(Cl)Cl>[Cl:28][C:29]1[CH:37]=[CH:36][C:32]([C:33]([NH:21][CH2:20][C:17]2[CH:18]=[CH:19][C:14]([S:11]([N:8]3[CH2:7][CH2:6][C:5]4([O:4][CH2:3][CH2:2][O:1]4)[CH2:10][CH2:9]3)(=[O:13])=[O:12])=[CH:15][CH:16]=2)=[O:34])=[CH:31][CH:30]=1

Participants

7

Reactant 5

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 85014-Chlorobenzoyl chlorideHCID 218852-DimethylaminopyridineHCID 59772980HCID 59772980, compound

Product 1

HCID 86591406HCID 86591406, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-ylsulfonyl)phenyl]methanamine 7b (3.00 g, 10.1 mmol) was dissolved in DCM (20 ml), pyridine (976 μl, 12.1 mmol), 4-chlorobenzoyl chloride (1.41 ml, 11.1 mmol) and dimethylaminopyridine (catalytic amount) were added and the mixture was stirred at room temp overnight. Excess benzoylchloride was scavenged with aminomethyl-PS (2.0 g, 2.2 mmol) by shaking for 2 h. The resin was filtered off and washed with DCM (20 ml). The combined filtrates were washed with saturated aqueous citric acid (20 ml), dried over magnesium sulphate and evaporated to dryness to yield 2.7 g (59%) sulfonamide 4-chloro-N-[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-ylsulfonyl)benzyl]benzamide 7c in >90% purity (LC-MS).

Workup

  1. stirringby shaking for 2 h
  2. filtrationThe resin was filtered off
  3. washwashed with DCM (20 ml)
  4. washThe combined filtrates were washed with saturated aqueous citric acid (20 ml)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-a413efd06d3c4f6a8394fa6877e809d1
Source dataset
uspto-grants-2008_08
Patent number
US07417058B2

Reaction notes

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