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

HRID 216015
Notes
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Reaction equation

HRID 216015 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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, 5H), 7.40-7.42 (m, 1 H), 7.26-7.29 (m, 1H), 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-36b7355bba264c8fa9818ddd034720ec
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08193191B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes