Oxindole → HCID 86584969, compound

HRID 1369688Notes

Reaction equation

HRID 1369688 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH:12][C@H:13]([C:15]([OH:17])=O)[CH3:14])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1.[NH2:18][CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22](C2C=CN=CC=2)[NH:21][C:20]1=[O:35].N1C2C(=CC=CC=2)CC1=O>>[F:8][C:6]1[CH:5]=[C:4]([CH2:9][C:10]([NH:12][C@H:13]([C:15]([C:19]2([NH2:18])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:21]([CH3:22])[C:20]2=[O:35])=[O:17])[CH3:14])=[O:11])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 3

HCID 321710OxindoleHCID 12135350(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoic acidHCID 223127504-Amino-1-(pyrid-4-yl)-1,2,3,4-tetrahydroisoquinolin-3-one

Product 1

HCID 86584969HCID 86584969, compound

Procedure

Following General Procedure I above using N-(3,5-difluorophenylacetyl)-L-alanine (Example B) and 3-amino-1-methyl-2-indolinone monohydrochloride (Example 5-B), the title compound, as a ˜1:1 diastereomeric mixture at C3 of the indolinone, was prepared as a white solid having a decomposition point of 215-220° C. Purification was by flash chromatography eluting with 3:1 CH2Cl2/EtOAc gradient to straight EtOAc followed by recrystalization from CHCl3. Rf=0.16 and 0.22 (EtOAc).

Sources & evidence

ORD record
ord-2ce7a146ca174b7a94c01dfaa8f188c7
Source dataset
uspto-grants-2003_06
Patent number
US06579867B2

Reaction notes

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