Isopropylamine → HCID 131724915, compound

HRID 1353826Notes

Reaction equation

HRID 1353826 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.Cl.CN(C)[CH2:31][CH2:32][CH2:33]N=C=NCC.[CH:40]([NH2:43])([CH3:42])[CH3:41]>CN(C)C=O>[O:23]1[C:22]2[CH:27]=[CH:26][CH:33]=[CH:32][C:31]=2[CH:25]=[C:24]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:43][CH:40]([CH3:42])[CH3:41])=[O:21])=[CH:15][CH:14]=2)[CH:10]=[N:11]1

Participants

5

Reactant 3

HCID 6363Isopropylamine2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22480189HCID 22480189, compound

Product 1

HCID 131724915HCID 131724915, compoundYield 199.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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-ethylcarbodiimide 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-6969cc9e2fdc4c4fa674ee87a7c5a529
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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