HCID 18976173, compound → HCID 131720826, compound

HRID 2393610Notes

Reaction equation

HRID 2393610 reaction equation
[NH2:1][C:2]1([CH2:21][CH2:22][C:23]#[N:24])[C:10]2[C:5](=[CH:6][C:7]([O:11][CH3:12])=[CH:8][CH:9]=2)[N:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[C:3]1=[O:20].O.[C:26]([C:34]([C:49]([OH:51])=[O:50])([OH:48])[C:35]([C:40](=[O:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([OH:39])[C:36]([OH:38])=[O:37])(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(OCC)(=O)C>[C:40]([C:35]([C:36]([OH:38])=[O:37])([OH:39])[C:34]([C:26](=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([OH:48])[C:49]([OH:51])=[O:50])(=[O:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.[NH2:1][C:2]1([CH2:21][CH2:22][C:23]#[N:24])[C:10]2[C:5](=[CH:6][C:7]([O:11][CH3:12])=[CH:8][CH:9]=2)[N:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[C:3]1=[O:20]

Participants

4

Reactant 2

HCID 18976173HCID 18976173, compoundHCID 24820425HCID 24820425, compound

Product 1

HCID 131720826HCID 131720826, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

70.70 g of the crude product of 3-[3-amino-1-(2-fluorophenyl)-2,3-dihydro-6-methoxy-2-oxo-1H-indol-3-yl]propanenitrile was dissolved in 250 ml of ethyl acetate. To this solution was added dropwise a solution of 51.21 g of (+)-dibenzoyltartaric acid monohydrate in 150 ml of ethyl acetate under ice cooling. The resulting crystals were collected by filtration and washed with water with ethyl acetate to afford 3-[3-amino-1-(2-fluorophenyl)-2,3-dihydro-6-methoxy-2-oxo-1H-indol-3-yl]propanenitrile (+)-dibenzoyltartrate (41.13 g) as pale yellow crystals, which was dissolved in 180 ml of hot methanol, concentrated, and triturated with ethyl acetate to afford 34.02 g of the above salt as colorless crystals (yield: 22%). [α]D25 : +50.0° (c=0.420, methanol). Melting point 155° to 157° C.

Workup

  1. filtrationThe resulting crystals were collected by filtration
  2. washwashed with water with ethyl acetate

Sources & evidence

ORD record
ord-d359dfc215e0494a9cb5ba4676dcaa33
Source dataset
uspto-grants-1998_09
Patent number
US05807883

Reaction notes

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