3-Fluorophenyl isocyanate → (S)-Methyl 2-(5-(4-(3-(3-fluorophenyl)ureido)phenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

HRID 403866Notes

Reaction equation

HRID 403866 reaction equation
FC1C=CC([NH:8][C:9](=[O:35])[NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[C:22](=[O:26])[N:21]([C@@H:27]([CH:32]([CH3:34])[CH3:33])[C:28]([O:30][CH3:31])=[O:29])[CH2:20]4)=[CH:13][CH:12]=2)=CC=1.NC1C=CC(C2C=C3C(=CC=2)C(=O)N([C@@H](C(C)C)C(OC)=O)C3)=CC=1.[F:61][C:62]1[CH:63]=[C:64](N=C=O)[CH:65]=[CH:66][CH:67]=1>>[F:61][C:62]1[CH:67]=[C:66]([NH:8][C:9](=[O:35])[NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[C:22](=[O:26])[N:21]([C@@H:27]([CH:32]([CH3:33])[CH3:34])[C:28]([O:30][CH3:31])=[O:29])[CH2:20]4)=[CH:13][CH:12]=2)[CH:65]=[CH:64][CH:63]=1

Participants

4

Reactant 3

HCID 1230643-Fluorophenyl isocyanateHCID 123620640(S)-Methyl 2-(5-(4-(3-(4-fluorophenyl)ureido)phenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoateHCID 131731499(S)-Methyl 2-(5-(4-aminophenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Product 1

HCID 131731502(S)-Methyl 2-(5-(4-(3-(3-fluorophenyl)ureido)phenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Procedure

The compound of example 228 was prepared analogous to compound of example 224 by reaction of compound of example 223 with 3-fluoro phenyl isocyanate. The compound of example 228 was used directly without isolation for the preparation of compound of example 229.

Sources & evidence

ORD record
ord-129b0b81bf97427d973aa086ce50dfa1
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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