Ethylmorpholine → 4-Chloro-7-[(1,1-dioxido-4-thiomorpholinyl)carbonyl]-1-methyl-1H-pyrrolo[3,2-c]pyridine

HRID 733726ノート

反応式

HRID 733726 の反応式
[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][N:10]([CH3:11])[C:6]=2[C:5]([C:12]([OH:14])=O)=[CH:4][N:3]=1.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N1CCOCC1)C.Cl.[NH:45]1[CH2:50][CH2:49][S:48](=[O:52])(=[O:51])[CH2:47][CH2:46]1>CN(C)C=O.O>[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][N:10]([CH3:11])[C:6]=2[C:5]([C:12]([N:45]2[CH2:50][CH2:49][S:48](=[O:52])(=[O:51])[CH2:47][CH2:46]2)=[O:14])=[CH:4][N:3]=1

参加物

8

反応物 5

HCID 7525EthylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 12324096Thiomorpholine 1,1-dioxide hydrochlorideHCID 578409034-Chloro-1-methyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acid

生成物 1

HCID 578409984-Chloro-7-[(1,1-dioxido-4-thiomorpholinyl)carbonyl]-1-methyl-1H-pyrrolo[3,2-c]pyridine収率 80.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-chloro-1-methyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acid (726 mg) in dimethylformamide (12 ml) was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (0.73 g), 1-hydroxybenzotriazole (0.52 g), N-ethylmorpholine (0.48 ml) and thiomorpholine 1,1-dioxide hydrochloride (0.66 g). The solution was stirred at room temperature overnight. The reaction was diluted with water and extracted three times with ethyl acetate. The ethyl acetate layers were combined, washed with saturated sodium chloride solution and dried (MgSO4) then evaporated. The residue was triturated with diethyl ether/n-hexane and filtered to afford the title compound as an off-white solid (0.907 g).

後処理

  1. extractionextracted three times with ethyl acetate
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. customthen evaporated
  5. customThe residue was triturated with diethyl ether/n-hexane
  6. filtrationfiltered

出典と根拠

ORDレコード
ord-8569668736d3408f894c12450a0682af
出典データセット
uspto-grants-2009_09
特許番号
US07589206B2

反応ノート

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