Trifluoroacetic acid → 2-(4-amino-1-(3,4-dimethoxyphenyl)butyl)-4-(4-((R)-1-phenylethyl)piperazin-1-yl)isoindoline-1,3-dione

HRID 606020Notes

Reaction equation

HRID 606020 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][CH:11]([C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[C:39]([O:45][CH3:46])[CH:38]=1)[N:12]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2[N:22]2[CH2:27][CH2:26][N:25]([C@@H:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH3:29])[CH2:24][CH2:23]2)[C:13]1=[O:36])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][CH2:8][CH2:9][CH2:10][CH:11]([N:12]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2[N:22]2[CH2:27][CH2:26][N:25]([C@@H:28]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH3:29])[CH2:24][CH2:23]2)[C:13]1=[O:36])[C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[C:39]([O:45][CH3:46])[CH:38]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23627305tert-butyl 4-(3,4-dimethoxyphenyl)-4-(1,3-dioxo-4-(4-((R)-1-phenylethyl)piperazin-1-yl)isoindolin-2-yl)butylcarbamate

Product 1

HCID 236272512-(4-amino-1-(3,4-dimethoxyphenyl)butyl)-4-(4-((R)-1-phenylethyl)piperazin-1-yl)isoindoline-1,3-dioneYield 10.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 10-mL round bottom flask was charge with Compound 65 (0.15 g, 2.0 mmol) and dichloromethane (2.0 mL). Trifluoroacetic acid (0.5 mL) was added and the mixture was stirred at room temperature for 3 h. The mixture was concentrated in vacuo to give Compound 66 (113 mg) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 7.63-7.69 (m, 1H), 7.50-7.56 (m, 5H), 7.40-7.42 (m, 1H), 7.26-7.29 (m, 1H), 7.13-7.18 (m, 1H), 7.02-7.06 (m, 1H), 6.88-6.92 (m, 1H), 5.25 (q, J=7.0 Hz, 1H), 4.47 (q, J=6.8 Hz, 1H), 3.85 (s, 3H), 3.80 (s, 3H), 3.47-3.60 (m, 3H), 3.32-3.36 (m, 4H), 2.96-3.07 (m, 3H), 2.54-2.67 (m, 1H), 2.32-2.42 (m, 1H), 1.80 (d, J=6.8 Hz, 3H), and 1.64-1.69 (s, 2H); MS (ES+) 543 (M+1).

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-c833e1b91eac474192ada6ffd0b01fd0
Source dataset
uspto-grants-2011_03
Patent number
US07915260B2

Reaction notes

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