Water → 1H-Indazole-3-carboxylic acid [4-(2-oxo-pyrrolidin-1-yl)-phenyl]-amide

HRID 902187

Reaction equation

HRID 902187 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.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:24][CH2:23][CH2:22][C:21]2=[O:25])=[CH:16][CH:15]=1.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.O>C(Cl)Cl.CCN(CC)CC>[O:25]=[C:21]1[CH2:22][CH2:23][CH2:24][N:20]1[C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:10]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][N:2]=2)=[O:12])=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 78250Indazole-3-carboxylic acidHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 676146Pyrrolidinone, (4-aminophenyl)-

Product 1

HCID 102454411H-Indazole-3-carboxylic acid [4-(2-oxo-pyrrolidin-1-yl)-phenyl]-amide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 50 mg 1H-Indazole-3-carboxylic acid in 2 mL DCM and 0.2 mL NEt3, 108 mg 1-(4-Amino-phenyl)-pyrrolidin-2-one and 79 mg BOP-Cl were added at RT and the mixture was stirred for 16 h. After the addition of 5 mL water the mixture was filtered through a chem elut® cartridge by elution with ethyl acetate and then concentrated under reduced pressure. The residue was directly subjected to the subsequent alkylation reaction without further purification.

Workup

  1. filtrationwas filtered through a chem elut® cartridge by elution with ethyl acetate
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was directly subjected to the subsequent alkylation reaction without further purification

Sources & evidence

ORD record
ord-89eb368042e54fcd940629a11921534b
Source dataset
uspto-grants-2008_04
Patent number
US07365088B2

Linked notes

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