HCID 12362975, compound → HCID 131720827, compound

HRID 2393615Notes

Reaction equation

HRID 2393615 reaction equation
[NH2:1][C:2]1([CH2:21][CH2:22][C:23]#[N:24])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH3:12])[CH:9]=2)[N:4]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:3]1=[O:20].[C:25]([C:33]([C:48]([OH:50])=[O:49])([OH:47])[C:34]([C:39](=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([OH:38])[C:35]([OH:37])=[O:36])(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(OCC)(=O)C>[C:39]([C:34]([C:35]([OH:37])=[O:36])([OH:38])[C:33]([C:25](=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([OH:47])[C:48]([OH:50])=[O:49])(=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.[NH2:1][C:2]1([CH2:21][CH2:22][C:23]#[N:24])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH3:12])[CH:9]=2)[N:4]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:3]1=[O:20]

Participants

4

Reactant 2

HCID 12362975HCID 12362975, compoundHCID 18976158HCID 18976158, compound

Product 1

HCID 131720827HCID 131720827, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

43.7 g of 3-[3-amino-1-(4-fluorophenyl)-2,3-dihydro-5-methoxy-2-oxo-1H-indol-3-yl]propanenitrile and 40 g of (-)-dibenzoyltartaric acid were dissolved in 300 ml of ethyl acetate, and the solution was allowed to stand at room temperature overnight while stirring gently. Precipitated crystals were collected by filtration and recrystallized from ethyl acetate to afford 26.4 g of 3-[3-amino-1-(4-fluorophenyl)-2,3-dihydro-5-methoxy-2-oxo-1H-indol-3-yl]-propanenitrile (-)-dibenzoyltartrate. Melting point: 157° to 158.5° C. [α]D20 : +64.91° (c=0.228, methanol). EI-MS (m/z): 325 (M+). IR (Nujol) (cm-1): 1380, 1460, 1690, 1740, 2250.

Workup

  1. customPrecipitated crystals
  2. filtrationwere collected by filtration
  3. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d8e1b1b9de6a49afba7261e6ee0553f2
Source dataset
uspto-grants-1998_09
Patent number
US05807883

Reaction notes

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