Tris(hydroxymethyl)aminomethane → N-(2-(3-(3-methoxy-4-nitrophenyl)-1H-pyrazol-1-yl)ethyl)-5-methyl-1H-pyrazole-3-carboxamide

HRID 872490Notes

Reaction equation

HRID 872490 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[NH:4][N:3]=1.C1C=CC2N(O)N=NC=2C=1.N=C=N.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([C:34]2[CH:38]=[CH:37][N:36]([CH2:39][CH2:40][NH2:41])[N:35]=2)[CH:28]=[CH:29][C:30]=1[N+:31]([O-:33])=[O:32].C(O)C(N)(CO)CO>CN(C=O)C.C(Cl)Cl>[CH3:23][O:24][C:25]1[CH:26]=[C:27]([C:34]2[CH:38]=[CH:37][N:36]([CH2:39][CH2:40][NH:41][C:7]([C:5]3[CH:6]=[C:2]([CH3:1])[NH:3][N:4]=3)=[O:9])[N:35]=2)[CH:28]=[CH:29][C:30]=1[N+:31]([O-:33])=[O:32]

Participants

8

Reactant 5

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 757711-HydroxybenzotriazoleHCID 160435CarbodiimideHCID 67172143HCID 67172143, compoundHCID 178427254HCID 178427254, compound

Product 1

HCID 70657571N-(2-(3-(3-methoxy-4-nitrophenyl)-1H-pyrazol-1-yl)ethyl)-5-methyl-1H-pyrazole-3-carboxamideYield 33.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

3-Methylpyrazole-5-carboxylic acid (70.0 mg, 0.555 mmol), HOBt (85 mg, 0.629 mmol) and PS-carbodiimide (672 mg) were weighed in a glass vial. DCM (4 ml) and DMF (0.4 ml) were added. The mixture was stirred for 10 minutes. 2-(3-(3-methoxy-4-nitrophenyl)-1H-pyrazol-1-yl)ethanamine (97 mg, 0.370 mmol) was added and the mixture was stirred for 24 h. The solids were filtered off. PS-Trisamine (616 mg, 1.849 mmol) was added to the filtrate. The mixture was stirred for 2 h and filtered. The filtrate was concentrated and purified by flash chromatography (gradient of DCM:MeOH) to give 46 mg of the title compound. 1H-NMR (400 MHz; CDCl3): δ 2.35 (s, 3H), 3.92, (m, 2H), 4.05, (s, 3H), 4.40, (t, 2H), 6.57 (s, 1H), 6.61 (d, 1H), 7.31 (s, 1H), 7.40-7.43 (m, 1H), 7.47 (d, 1H), 7.62 (d, 1H), 7.96 (d, 1H), 9.94 (s, 1H).

Workup

  1. stirringthe mixture was stirred for 24 h
  2. filtrationThe solids were filtered off
  3. stirringThe mixture was stirred for 2 h
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by flash chromatography (gradient of DCM:MeOH)

Sources & evidence

ORD record
ord-304e555f4caa42dabde9030aab1a92c9
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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