Water → HCID 11494008, compound

HRID 2409804Notes

Reaction equation

HRID 2409804 reaction equation
Cl.CN(C)CCCN=C=NCC.[NH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23]3[O:27][C:26]([C:28]([OH:30])=O)=[CH:25][CH:24]=3)[CH:21]=2)[NH:16][N:15]=1.[OH:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=1)[CH2:35][NH2:36].O>CN(C=O)C>[OH:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=1)[CH2:35][NH:36][C:28]([C:26]1[O:27][C:23]([C:20]2[CH:21]=[C:22]3[C:17](=[CH:18][CH:19]=2)[NH:16][N:15]=[C:14]3[NH2:13])=[CH:24][CH:25]=1)=[O:30]

Participants

6

Reactant 4

HCID 962WaterHCID 7358943-(Aminomethyl)phenolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58985366HCID 58985366, compound

Product 1

HCID 11494008HCID 11494008, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

144 mg (0.75 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (DAPECI) are added to a solution of 146 mg (0.60 mmol) of 5-(3-amino-1H-indazol-5-yl)furan-2-carboxylic acid and 73.9 mg (0.60 mmol) of 3-hydroxybenzylamine in 1 ml of DMF, and the mixture is stirred at room temperature for 4 hours. Water is added to the reaction mixture, which is extracted with ethyl acetate. The organic phase is dried over sodium sulfate and evaporated, and the residue is purified by preparative HPLC, giving N-3-hydroxybenzyl-5-(3-amino-1H-indazol-5-yl)furan-2-carboxamide (“62”) as yellowish solid, ESI 349.

Workup

  1. extractionis extracted with ethyl acetate
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customevaporated
  4. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-43a9473171e74f6787ca543901f72759
Source dataset
uspto-grants-2014_08
Patent number
US08815924B2

Reaction notes

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