Malic Acid → HCID 68524517, compound

HRID 2191508Notes

Reaction equation

HRID 2191508 reaction equation
[CH2:1]([N:3]([CH2:30][CH3:31])[CH2:4][CH2:5][N:6]1[CH2:12][CH2:11][CH2:10][CH:9]2[NH:13][C:14](/[CH:17]=[C:18]3\[C:19](=[O:28])[NH:20][C:21]4[C:26]\3=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)=[C:15]([CH3:16])[CH:8]2[C:7]1=[O:29])[CH3:2].[OH:32][CH:33]([CH2:37][C:38]([OH:40])=[O:39])[C:34]([OH:36])=[O:35]>CO>[C:34]([OH:36])(=[O:35])[CH:33]([CH2:37][C:38]([OH:40])=[O:39])[OH:32].[CH2:30]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[CH2:12][CH2:11][CH2:10][CH:9]2[NH:13][C:14](/[CH:17]=[C:18]3\[C:19](=[O:28])[NH:20][C:21]4[C:26]\3=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)=[C:15]([CH3:16])[CH:8]2[C:7]1=[O:29])[CH3:31]

Participants

4

Reactant 2

HCID 525Malic AcidHCID 50908794HCID 50908794, compound

Product 1

HCID 68524517HCID 68524517, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(Z)-5-(2-Diethylamino-ethyl)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-methyl-3a,5,6,7,8,8a-hexahydro-1H-pyrrolo[3,2-c]azepin-4-one 1 (2.01 g, 4.75 mmol) obtained from Example 1 was dissolved in 279 ml of methanol under stirring, and added with 2-hydroxy-succinic acid (0.953 g, 7.11 mmol) to the solution in one portion. The orange solution was concentrated under reduced pressure, added with 45 ml of acetonitrile, heated to reflux for 30 minutes in an oil bath. The oil bath was then removed, and the reaction mixture was naturally cooled down to room temperature, filtered and dried to obtain the title compound (Z)-5-(2-diethylamino-ethyl)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-methyl-3a,5,6,7,8,8a-hexahydro-1H-pyrrolo[3,2-c]azepin-4-one malate 63 (2.02 g, yield 76.2%) as an orange solid.

Workup

  1. concentrationThe orange solution was concentrated under reduced pressure
  2. additionadded with 45 ml of acetonitrile
  3. temperatureheated
  4. temperatureto reflux for 30 minutes in an oil bath
  5. customThe oil bath was then removed
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-773844ef60194522b930bd665c84d199
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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