Methanol → N-[6-(1H-Indol-4-yl)-1-methyl-1H-indazol-4-yl]-2-pyridinecarboxamide

HRID 1616002Notes

Reaction equation

HRID 1616002 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:11]=[C:12]([NH2:20])[C:13]4[CH:14]=[N:15][N:16]([CH3:19])[C:17]=4[CH:18]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CCN(C(C)C)C(C)C.Cl.[N:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37](Cl)=[O:38].CO>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:18]=[C:17]4[C:13]([CH:14]=[N:15][N:16]4[CH3:19])=[C:12]([NH:20][C:37]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][N:31]=4)=[O:38])[CH:11]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 135033Picolinoyl Chloride HydrochlorideHCID 582680236-(1H-Indol-4-yl)-1-methyl-1H-indazol-4-amine

Product 1

HCID 44540780N-[6-(1H-Indol-4-yl)-1-methyl-1H-indazol-4-yl]-2-pyridinecarboxamideYield 23.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-(1H-Indol-4-yl)-1-methyl-1H-indazol-4-amine (70 mg, 0.27 mmol) was dissolved in DCM (3 ml) and treated with DIPEA (0.145 ml). 2-Pyridinecarbonyl chloride hydrochloride (59.5 mg, 0.34 mmol) was added and the reaction was stirred for 5 h. MeOH (2 ml) was added and the reaction stirred overnight. The solvent was evaporated and the residue was treated with DCM/Methanol (1:1, 2 ml) then evaporated to dryness. The product was dissolved in DMSO (2 ml) and purified by Mass Directed Automated Preparative HPLC (Method B). Fractions containing product were combined and dried to give the title compound (23 mg).

Workup

  1. stirringthe reaction stirred overnight
  2. customThe solvent was evaporated
  3. additionthe residue was treated with DCM/Methanol (1:1, 2 ml)
  4. customthen evaporated to dryness
  5. dissolutionThe product was dissolved in DMSO (2 ml)
  6. custompurified by Mass Directed Automated Preparative HPLC (Method B)
  7. additionFractions containing product
  8. customdried

Sources & evidence

ORD record
ord-3871c9899bb0483b8250bb552bb65e63
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

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