Dimethylformamide → HCID 131724915, compound

HRID 2183267Notes

Reaction equation

HRID 2183267 reaction equation
O1C2C=CC=CC=2C=C1[C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]([OH:21])=O)[CH:17]=2)[N:12]([CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[N:11]=1.[CH:28]([NH2:31])([CH3:30])[CH3:29].CN(C)[CH:34]=[O:35]>>[O:35]1[C:34]2[CH:19]=[CH:16][CH:15]=[CH:14][C:13]=2[CH:18]=[C:17]1[CH:27]1[CH2:26][CH2:25][CH2:24][O:23][CH:22]1[N:12]1[C:13]2[C:18](=[CH:17][C:16]([C:19]([NH:31][CH:28]([CH3:30])[CH3:29])=[O:21])=[CH:15][CH:14]=2)[CH:10]=[N:11]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 6363Isopropylamine2×HCID 22480189HCID 22480189, compound

Product 1

HCID 131724915HCID 131724915, compoundYield 81%

Procedure

To solution of 3-benzo[d]furan-2-yl-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carboxylic acid (190 mg, 0.52 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarboimide hydrochloride (109.3 mg, 0.57 mmol) in dimethylformamide was added isopropylamine (48 μL, 0.57 mmol) and the mixture allowed to stir under a nitrogen atmosphere for two days. An additional 2 equivalents of isopropylamine was added to the reaction and allowed to stir for another day. Solvent was removed and the reaction was extracted with ethyl acetate. The crude material was purified by preparative HPLC to yield the title compound (209 mg, 81% yield). ES-MS (m/z) 404 [M+1]+.

Workup

  1. stirringto stir for another day
  2. customSolvent was removed
  3. extractionthe reaction was extracted with ethyl acetate
  4. customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-b26a9b04e5604551a2cd4b94dc148e8a
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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