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

HRID 42326Notes

Reaction equation

HRID 42326 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, 1 H), 7.50-7.56 (m, 5 H), 7.40-7.42 (m, 1 H), 7.26-7.29 (m, 1 H), 7.13-7.18 (m, 1 H), 7.02-7.06 (m, 1 H), 6.88-6.92 (m, 1 H), 5.25 (q, J=7.0 Hz, 1 H), 4.47 (q, J=6.8 Hz, 1 H), 3.85 (s, 3 H), 3.80 (s, 3 H), 3.47-3.60 (m, 3 H), 3.32-3.36 (m, 4 H), 2.96-3.07 (m, 3 H), 2.54-2.67 (m, 1 H), 2.32-2.42 (m, 1 H), 1.80 (d, J=6.8 Hz, 3 H), and 1.64-1.69 (s, 2 H); MS (ES+) 543 (M+1).

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-3a079de870cd4eb7929361e000f356e1
Source dataset
uspto-grants-2013_09
Patent number
US08536174B2

Reaction notes

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