Furfurylamine → N-(furan-2-ylmethyl)-5-(isoquinolin-6-yl)-1,3,4-thiadiazol-2-amine

HRID 2075342ノート

反応式

HRID 2075342 の反応式
CS([C:5]1[S:9][C:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]=[N:15][CH:14]=[CH:13]3)=[N:7][N:6]=1)(=O)=O.CS(C1SC(C2C=C3C(=CC=2)C=NC=C3)=NN=1)=O.[O:38]1[CH:42]=[CH:41][CH:40]=[C:39]1[CH2:43][NH2:44]>CCOC(C)=O>[O:38]1[CH:42]=[CH:41][CH:40]=[C:39]1[CH2:43][NH:44][C:5]1[S:9][C:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]=[N:15][CH:14]=[CH:13]3)=[N:7][N:6]=1

参加物

5

反応物 3

HCID 3438FurfurylamineHCID 579918986-(5-(Methylsulfonyl)-1,3,4-thiadiazol-2-yl)isoquinolineHCID 670894316-(5-(Methylsulfinyl)-1,3,4-thiadiazol-2-yl)isoquinoline

生成物 1

HCID 57991934N-(furan-2-ylmethyl)-5-(isoquinolin-6-yl)-1,3,4-thiadiazol-2-amine収率 65%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

A stirred mixture of 6-(5-(methylsulfonyl)-1,3,4-thiadiazol-2-yl)isoquinoline and 6-(5-(methylsulfinyl)-1,3,4-thiadiazol-2-yl)isoquinoline (44 mg, 0.16 mmol) and furan-2-ylmethanamine (78 mg, 0.8 mmol) (commercially available from Acros Organics (Order Number 11980)) was heated at 80-100° C. for 3 hours. The resulting mixture was cooled to room temperature, diluted with EtOAc and washed with 2M aqueous Na2CO3 solution and water. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluting with gradients of EtOAc in hexanes) to provide N-(furan-2-ylmethyl)-5-(isoquinolin-6-yl)-1,3,4-thiadiazol-2-amine as an amphorous solid (32 mg, 65%). LCMS (M+H) 309.3 calc for C16H13N4OS 309.1. 1H NMR (300 MHz, DMSO-d6): δ ppm 9.34 (s, 1H), 8.54 (m, 2H), 8.29 (s, 1H), 8.17 (m, 2H), 7.92 (d, J=5.8 Hz, 1H), 7.64 (s, 1H), 6.43 (m, 2H), 4.58 (d, J=5.2 Hz, 2H).

後処理

  1. temperatureThe resulting mixture was cooled to room temperature
  2. washwashed with 2M aqueous Na2CO3 solution and water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel (eluting with gradients of EtOAc in hexanes)

出典と根拠

ORDレコード
ord-cd8d0714a15041bcbd8132d1c3f671fa
出典データセット
uspto-grants-2011_04
特許番号
US07919504B2

反応ノート

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