Potassium Carbonate → 2-(pentylthio)-N-(2-thienylmethyl)-3-quinoline carboxamide

HRID 1949167ノート

反応式

HRID 1949167 の反応式
[SH:1][C:2]1[C:11]([C:12]([NH:14][CH2:15][C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>CN(C=O)C>[CH2:28]([S:1][C:2]1[C:11]([C:12]([NH:14][CH2:15][C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)[CH2:29][CH2:30][CH2:31][CH3:32]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 123351-IodopentaneHCID 178523047HCID 178523047、化合物

生成物 1

HCID 469115432-(pentylthio)-N-(2-thienylmethyl)-3-quinoline carboxamide収率 40%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 300 mg (1.0 mmol) 2-mercapto-N-(thiophen-2-ylmethyl)quinoline-3-carboxamide (precursor VVV02) in DMF (2.3 ml) was mixed with 151 mg (1.1 mmol) K2CO3 at room temperature and stirred for 30 min. Then 131 μl (1.0 mmol) 1-iodopentane were added and the mixture was stirred for a further 3 days at RT. Then the mixture was concentrated to small volume under vacuum and the residue was taken up with EE and washed with water. The aqueous phase was extracted with EE and the combined organic phases were dried over MgSO4, filtered and concentrated to small volume under vacuum. Crystallisation of the residue from EE yielded 146 mg (0.4 mmol, 39%) 2-(pentylthio)-N-(2-thienylmethyl)-3-quinoline carboxamide. MS: m/z 371.1 [M+H]+.

後処理

  1. stirringthe mixture was stirred for a further 3 days at RT
  2. concentrationThen the mixture was concentrated to small volume under vacuum
  3. washwashed with water
  4. extractionThe aqueous phase was extracted with EE
  5. dry with materialthe combined organic phases were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to small volume under vacuum
  8. customCrystallisation of the residue from EE

出典と根拠

ORDレコード
ord-937ccbab42934eb6976655d3caf35912
出典データセット
uspto-grants-2013_03
特許番号
US08399673B2

反応ノート

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