Triethylamine → 2-Chloro-4-[3-(3-nitro-benzenesulfonylamino)-propylamino]-pyrimidine-5-carboxylic acid-tert-butylamide

HRID 970425

Reaction equation

HRID 970425 reaction equation
[C:1]([NH:5][C:6]([C:8]1[C:9](Cl)=[N:10][C:11]([Cl:14])=[N:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:16][CH2:17][CH2:18][CH2:19][NH:20][S:21]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[CH:25]=1)(=[O:23])=[O:22].C(N(CC)CC)C>C1COCC1>[C:1]([NH:5][C:6]([C:8]1[C:9]([NH:16][CH2:17][CH2:18][CH2:19][NH:20][S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[CH:25]=2)(=[O:22])=[O:23])=[N:10][C:11]([Cl:14])=[N:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 223267522,4-Dichloro-pyrimidine-5-carboxylic acid-tert-butylamideHCID 24711458N-(3-amino-propyl)-3-nitro-benzenesulfonamide

Product 1

HCID 590203532-Chloro-4-[3-(3-nitro-benzenesulfonylamino)-propylamino]-pyrimidine-5-carboxylic acid-tert-butylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.95 g (3.83 mmol) of 2,4-dichloro-pyrimidine-5-carboxylic acid-tert-butylamide in 6 ml of THF is mixed at room temperature while being stirred with a suspension that consists of 1.00 g (3.86 mmol) of N-(3-amino-propyl)-3-nitro-benzenesulfonamide in 9 ml of THF/0.55 ml of triethylamine. After 19 hours, the precipitate that is formed is suctioned off and washed with ethyl acetate. The filtrate is spun in, and the residue that is formed is purified by chromatography (hexane/ethyl acetate 2:1, Flashmaster II). 0.79 g (1.67 mmol, corresponding to 44% of theory) of the product is obtained.

Workup

  1. customthe precipitate that is formed
  2. washwashed with ethyl acetate
  3. customis formed
  4. customis purified by chromatography (hexane/ethyl acetate 2:1, Flashmaster II)
  5. custom0.79 g (1.67 mmol, corresponding to 44% of theory) of the product is obtained

Sources & evidence

ORD record
ord-0db5b4a523594f119ebe43eb544973a3
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Linked notes

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