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

HRID 48456

反応式

HRID 48456 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8658b4d0de8f49fdbec462b7b9b6e592
出典データセット
uspto-grants-2004_03
特許番号
US06703397B2

関連ノート

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