Trifluoroacetic acid → HCID 58318016, compound

HRID 1505041Notes

Reaction equation

HRID 1505041 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:10]=2[CH2:11][CH2:12][N:13]([CH2:20][C@H:21]2[CH2:25][O:24]C(C)(C)[O:22]2)[C:14]3=[O:19])=[CH:4][C:3]=1[C:28]1[NH:29][C:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:31][N:32]=1.C(O)(C(F)(F)F)=O>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:10]=2[CH2:11][CH2:12][N:13]([CH2:20][C@H:21]([OH:22])[CH2:25][OH:24])[C:14]3=[O:19])=[CH:4][C:3]=1[C:28]1[NH:29][C:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:31][N:32]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58318062HCID 58318062, compound

Product 1

HCID 58318016HCID 58318016, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-5-(4-chloro-3-(5-phenyl-1H-imidazol-2-yl)phenylamino)-2-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-3,4-dihydroisoquinolin-1(2H)-one (210 mg, 0.40 mmol) in THF (1.6 ml) and water (0.4 ml) is added TFA (0.1 ml) at room temperature, and the reaction mixture is stirred for 18 hours. The reaction mixture is concentrated to dryness by rotary evaporation and the crude product is purified by preparative HPLC to afford (S)-5-(4-Chloro-3-(5-phenyl-1H-imidazol-2-yl)phenylamino)-2-(2,3-dihydroxypropyl)-3,4-dihydroisoquinolin-1(2H)-one as an off-white solid. LC-MS m/z: 489.1 (M+1); 1H NMR 400 MHz (CDCl3) δ 7.76 (d, 1H, J=7.6 Hz), 7.67-7.63 (m, 3H), 7.40-7.32 (m, 4H), 7.27-7.20 (m, 3H), 6.71-6.68 (m, 1H), 3.89-3.87 (m, 1H), 3.66-3.53 (m, 6H), 2.82 (t, 2H, J=6.8 Hz).

Workup

  1. concentrationThe reaction mixture is concentrated to dryness by rotary evaporation
  2. customthe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-5cbc20fdc6384fb4a0551fd8054b5dc9
Source dataset
uspto-grants-2015_12
Patent number
US09216964B2

Reaction notes

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