Dichloromethane → 1H-Indazole-3-carboxylic acid {2-[5-(3,4-dichlorophenyl)-furan-2-yl]ethyl}-amide

HRID 872449Notes

Reaction equation

HRID 872449 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=O)=[N:2]1.C1CCC(N=C=NC2CCCCC2)CC1.[Cl:28][C:29]1[CH:30]=[C:31]([C:36]2[O:40][C:39]([CH2:41][CH2:42][NH2:43])=[CH:38][CH:37]=2)[CH:32]=[CH:33][C:34]=1[Cl:35].C(Cl)Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl.CN(C=O)C>[Cl:28][C:29]1[CH:30]=[C:31]([C:36]2[O:40][C:39]([CH2:41][CH2:42][NH:43][C:10]([C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][N:2]=3)=[O:12])=[CH:38][CH:37]=2)[CH:32]=[CH:33][C:34]=1[Cl:35]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 78250Indazole-3-carboxylic acidHCID 547757822-(5-(3,4-Dichlorophenyl)furan-2-yl)ethanamine

Product 1

HCID 671701131H-Indazole-3-carboxylic acid {2-[5-(3,4-dichlorophenyl)-furan-2-yl]ethyl}-amideYield 34.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

Indazole-3-carboxylic acid (30 mg; 0.182 mmol), DCC (56 mg, 0.273 mmol) and DMAP (2 mg) were dissolved in DCM:DMF (1:1, 4 ml). 2-(5-(3,4-dichlorophenyl)furan-2-yl)ethanamine (46 mg, 0.182 mmol) was added and the reaction mixture was stirred for overnight at RT. DCM (30 ml) was added and organic layer washed with water (3×15 ml). Combined organic phases were dried over Na2SO4, evaporated and purified by chromatography (silica column, eluent: 1% MeOH/DCM) to give 25 mg (34%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 3.00 (t, 2H), 3.63 (q, 2H), 6.37 (d, 1H), 7.02 (d, 1H), 7.23 (t, 1H), 7.41 (t, 1H), 7.60 (d, 1H), 7.61 (d, 2H), 7.85 (d, 1H), 8.16 (d, 1H), 8.54 (d, 1H), 13.56 (s, 1H).

Workup

  1. washorganic layer washed with water (3×15 ml)
  2. dry with materialCombined organic phases were dried over Na2SO4
  3. customevaporated
  4. custompurified by chromatography (silica column, eluent: 1% MeOH/DCM)

Sources & evidence

ORD record
ord-c009fb7712ab431e8de8bda8c0aa25f5
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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