5-Amino-2,3-dihydro-isoindol-1-one → (R)-1-((R)-4-(3,5-bis(trifluoromethyl)phenyl)-3-oxomorpholin-2-yl)-2-oxo-2-(1-oxoisoindolin-5-ylamino)ethyl acetate

HRID 876596

Reaction equation

HRID 876596 reaction equation
[C:1]([O:4][C@H:5]([C@H:9]1[O:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=2)[C:10]1=[O:29])[C:6](O)=[O:7])(=[O:3])[CH3:2].[NH2:30][C:31]1[CH:32]=[C:33]2[C:37](=[CH:38][CH:39]=1)[C:36](=[O:40])[NH:35][CH2:34]2>>[C:1]([O:4][C@H:5]([C@H:9]1[O:14][CH2:13][CH2:12][N:11]([C:15]2[CH:16]=[C:17]([C:25]([F:26])([F:28])[F:27])[CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=2)[C:10]1=[O:29])[C:6](=[O:7])[NH:30][C:31]1[CH:32]=[C:33]2[C:37](=[CH:38][CH:39]=1)[C:36](=[O:40])[NH:35][CH2:34]2)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 219562395-Amino-2,3-dihydro-isoindol-1-oneHCID 58181384HCID 58181384, compound

Product 1

HCID 58181829(R)-1-((R)-4-(3,5-bis(trifluoromethyl)phenyl)-3-oxomorpholin-2-yl)-2-oxo-2-(1-oxoisoindolin-5-ylamino)ethyl acetateYield 81.5%

Procedure

According to the Step 70-5 in the synthetic method for EXAMPLE 70, compound 73-3 (65 mg) was used instead of compound 70-4 to couple to 5-aminoisoindolin-1-one (25 mg) to obtain compound 74-1 (69 mg) as a white solid after reverse-phase (C18) purification.

Sources & evidence

ORD record
ord-996ee7fa4037479297e79bbc58f35ec1
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Linked notes

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