2-(3-Oxobutyl)isoindoline-1,3-dione → 3-[[1-(3-Amino-1-methyl-propyl)-piperidin-4-yl]-(5-chloro-2-fluoro-benzyl)-amino]-benzoic acid methyl ester

HRID 1726225Notes

Reaction equation

HRID 1726225 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:25][C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=2[F:33])[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([O:23][CH3:24])=[O:22])[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.O=[C:35]([CH3:49])[CH2:36][CH2:37][N:38]1C(=O)C2C(=CC=CC=2)C1=O>>[CH3:24][O:23][C:21](=[O:22])[C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([N:14]([CH:11]2[CH2:12][CH2:13][N:8]([CH:35]([CH3:49])[CH2:36][CH2:37][NH2:38])[CH2:9][CH2:10]2)[CH2:25][C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=2[F:33])[CH:16]=1

Participants

3

Reactant 2

HCID 2907282-(3-Oxobutyl)isoindoline-1,3-dioneHCID 689717204-[(5-Chloro-2-fluoro-benzyl)-(3-methoxycarbonyl-phenyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 689688583-[[1-(3-Amino-1-methyl-propyl)-piperidin-4-yl]-(5-chloro-2-fluoro-benzyl)-amino]-benzoic acid methyl ester

Procedure

Using general procedure C with the carbamate (910 mg, 1.91 mmol), then general procedure B with the resulting amine and 2-(3-oxo-butyl)-isoindole-1,3-dione (565 mg, 2.60 mmol) and then using general procedure D gave 3-[[1-(3-amino-1-methyl-propyl)-piperidin-4-yl]-(5-chloro-2-fluoro-benzyl)-amino]-benzoic acid methyl ester as a white foam (473 mg, 56% over 3 steps).

Sources & evidence

ORD record
ord-9727ef4fa60a40e088d90e3a039b2db5
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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