1,1'-Thiocarbonyldiimidazole → HCID 86608390, compound

HRID 1844953Notes

Reaction equation

HRID 1844953 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH2:11])[N:2]=1.N1([C:17]([N:19]2[CH:23]=[CH:22][N:21]=C2)=[S:18])C=CN=C1.[CH3:24][O:25][C:26](=[O:35])[C:27]1C=C[CH:30]=[C:29](N)[C:28]=1N>C1COCC1.CCN(C(C)C)C(C)C>[CH3:24][O:25][C:26](=[O:35])[C:27]1[CH:28]=[CH:29][CH:30]=[C:23]([NH:19][C:17]([NH:11][C:3]2[N:2]=[CH:1][C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][CH:9]=3)=[S:18])[C:22]=1[NH2:21]

Participants

6

Reactant 3

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 311869Isoquinolin-3-AmineHCID 5718252,3-Diaminobenzoic acid methyl ester

Product 1

HCID 86608390HCID 86608390, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

To a stirring solution of 0.86 g (6.0 mmol) of isoquinolin-3-ylamine in dry THF (30 mL) was added 1.25 g (7.0 mmol) of di-imidazol-1-yl-methanethione. The reaction mixture was refluxed for 30 min. After cooling to room temperature, a solution of 1.7 g (10 mmol) of 2,3-diamino-benzoic acid methyl ester (for synthesis see example 1) in THF (40 mL) and DIEA (2 mL) was added subsequently. The reaction mixture was stirred at room temperature for 1 h and diluted with hexanes (40 mL). The resulting precipitate was filtered. The solid was washed with water and ether and dried under vacuum to give 2-amino-3-(3-isoquinolin-3-yl-thioureido)-benzoic acid methyl ester as a solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 30 min
  2. filtrationThe resulting precipitate was filtered
  3. washThe solid was washed with water and ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-e5a3d4cd3b504e8b83f18b03632da5c7
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

Loading…