Dimethylsulphamoyl chloride → 6-(2,4-Diamino-pyrimidin-5-ylmethyl)-4-ethoxy-indole-1-sulfonic Acid Dimethylamide

HRID 48456

반응식

HRID 48456 반응식
CC([O-])(C)C.[K+].[CH2:7]([O:9][C:10]1[CH:18]=[C:17]([CH2:19][C:20]2[C:21]([NH2:27])=[N:22][C:23]([NH2:26])=[N:24][CH:25]=2)[CH:16]=[C:15]2[C:11]=1[CH:12]=[CH:13][NH:14]2)[CH3:8].[CH3:28][N:29]([CH3:34])[S:30](Cl)(=[O:32])=[O:31]>CN(C)C=O>[CH3:28][N:29]([CH3:34])[S:30]([N:14]1[C:15]2[C:11](=[C:10]([O:9][CH2:7][CH3:8])[CH:18]=[C:17]([CH2:19][C:20]3[C:21]([NH2:27])=[N:22][C:23]([NH2:26])=[N:24][CH:25]=3)[CH:16]=2)[CH:12]=[CH:13]1)(=[O:32])=[O:31]

참가 물질

5

반응물 3

HCID 83372Dimethylsulphamoyl chlorideHCID 227429195-(4-Ethoxy-1H-indol-6-ylmethyl)-pyrimidine-2,4-diamineHCID 23665647Potassium tert-butoxide

생성물 1

HCID 699205526-(2,4-Diamino-pyrimidin-5-ylmethyl)-4-ethoxy-indole-1-sulfonic Acid Dimethylamide수율 53%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Potassium tert-butylate (42 mg, 0.37 mmol) was added to a solution of 5-(4-ethoxy-1H-indol-6-ylmethyl)-pyrimidine-2,4-diamine (Example 1; 100 mg, 0.353 mmol) in N,N-dimethylformamide (5 mL). After 15 min dimethylsulfamoyl chloride (53 mg, 0.37 mmol) was added, then after 30 min the solvent was distilled off and the residue partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with brine, dried (MgSO4), and evaporated. Suspension of the residue in ether and collection of the precipitate afforded the title compound (73 mg, 53%). Off-white solid.

후처리

  1. distillationafter 30 min the solvent was distilled off
  2. customthe residue partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. additionSuspension of the residue in ether
  7. customcollection of the precipitate

출처 및 근거

ORD 기록
ord-8658b4d0de8f49fdbec462b7b9b6e592
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06703397B2

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