2-Furancarbonyl chloride → HCID 58356403, compound

HRID 244736Notes

Reaction equation

HRID 244736 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:11]=[C:12]([NH2:25])[C:13]4[C:17]([CH:18]=3)=[N:16][N:15](C3CCCCO3)[CH:14]=4)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CCN(C(C)C)C(C)C.[O:35]1[CH:39]=[CH:38][CH:37]=[C:36]1[C:40](Cl)=[O:41]>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][NH:16]4)=[C:12]([NH:25][C:40]([C:36]4[O:35][CH:39]=[CH:38][CH:37]=4)=[O:41])[CH:11]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 682422-Furancarbonyl chlorideHCID 81531DiisopropylethylamineHCID 582679956-(1H-Indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine

Product 1

HCID 58356403HCID 58356403, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(1H-indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (50 mg) in DCM (1 ml) was added DIPEA (131 μl) followed by 2-furancarbonyl chloride (39 mg) (available from ABCR) and the mixture stirred at RT for 1 h, then the solvent was removed. To a mixture of the residue in methanol (2 ml) was added 4M hydrochloric acid in 1,4-dioxane (2 ml) and the mixture stirred at RT for 2 h. Purification of the residue by mass directed preparative HPLC (Method A), followed by freeze drying gave the title compound as an off white solid (13 mg).

Workup

  1. customthe solvent was removed
  2. additionTo a mixture of the residue in methanol (2 ml)
  3. additionwas added 4M hydrochloric acid in 1,4-dioxane (2 ml)
  4. stirringthe mixture stirred at RT for 2 h
  5. customPurification of the residue by mass
  6. customdrying

Sources & evidence

ORD record
ord-5736065300194bf4afe1777ed4e6d08c
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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