Trifluoroacetic acid → HCID 59374985, compound

HRID 1811166Notes

Reaction equation

HRID 1811166 reaction equation
CC1(C)[O:6][CH:5]([CH2:7][O:8][C:9]2[CH:21]=[C:20]3[C:12]([C:13]4[C:14]([C:25]5[CH:30]=[CH:29][CH:28]=[C:27]([N:31]6[CH2:39][C:38]7[C:33](=[CH:34][C:35]([CH3:40])=[CH:36][CH:37]=7)[C:32]6=[O:41])[C:26]=5[CH3:42])=[CH:15][CH:16]=[C:17]([C:22]([NH2:24])=[O:23])[C:18]=4[NH:19]3)=[CH:11][CH:10]=2)[CH2:4][O:3]1.C(O)(C(F)(F)F)=O>CO.CS(C)=O>[OH:6][CH:5]([CH2:4][OH:3])[CH2:7][O:8][C:9]1[CH:21]=[C:20]2[C:12]([C:13]3[C:14]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([N:31]5[CH2:39][C:38]6[C:33](=[CH:34][C:35]([CH3:40])=[CH:36][CH:37]=6)[C:32]5=[O:41])[C:26]=4[CH3:42])=[CH:15][CH:16]=[C:17]([C:22]([NH2:24])=[O:23])[C:18]=3[NH:19]2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59375132HCID 59375132, compound

Product 1

HCID 59374985HCID 59374985, compoundYield 33.8%

Reagents, catalysts & solvents 1

HCID 22036561Dimethyl sulfoxide methanolSolvent

Procedure

A solution of racemic 7-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-4-(2-methyl-3-(6-methyl-1-oxoisoindolin-2-yl)phenyl)-9H-carbazole-1-carboxamide (Example 44-4, 30 mg, 0.052 mmol) in methanol-DMSO was treated with TFA (0.5 mL) and the solution was stirred overnight at rt. The mixture was concentrated and purified by preparative HPLC to provide 7-(2,3-dihydroxypropoxy)-4-(2-methyl-3-(6-methyl-1-oxoisoindolin-2-yl)phenyl)-9H-carbazole-1-carboxamide as a white solid (9.4 mg, 32%). 1H NMR (400 MHz, DMSO-d6) δ 11.39 (1 H, s), 8.16 (1 H, br. s.), 7.94 (1 H, d, J=7.7 Hz), 7.54-7.65 (3 H, m), 7.49 (3 H, t, J=7.9 Hz), 7.25-7.38 (2 H, m), 6.99 (1 H, d, J=7.7 Hz), 6.92 (1 H, d, J=8.8 Hz), 6.60 (1 H, d, J=1.3 Hz), 4.82-5.01 (3 H, m), 4.60-4.71 (1 H, m), 3.96-4.08 (1 H, m), 3.76-3.96 (2 H, m), 3.48 (2H, t, J=5.6 Hz), 2.44 (3 H, s), 1.77-1.88 (3 H, m). Mass spectrum m/z 536.1 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-f583fd46aa8f41e78516e8451e2dd321
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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