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

HRID 2075342Notes

Reaction equation

HRID 2075342 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-cd8d0714a15041bcbd8132d1c3f671fa
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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