Sodium Hydroxide → HCID 25144892, compound

HRID 576289Notes

Reaction equation

HRID 576289 reaction equation
[C:1]([NH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12]([O:16][CH2:17][CH2:18][CH2:19][C:20]1[C:28]3[C:23](=[C:24]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[CH3:35])[CH:25]=[CH:26][CH:27]=3)[NH:22][C:21]=1[C:36]([O:38]CC)=[O:37])=[CH:11][CH:10]=[CH:9]2)(=[O:4])[CH:2]=[CH2:3].[OH-].[Na+]>O1CCCC1.CO>[C:1]([NH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12]([O:16][CH2:17][CH2:18][CH2:19][C:20]1[C:28]3[C:23](=[C:24]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[CH3:35])[CH:25]=[CH:26][CH:27]=3)[NH:22][C:21]=1[C:36]([OH:38])=[O:37])=[CH:11][CH:10]=[CH:9]2)(=[O:4])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68939844HCID 68939844, compound

Product 1

HCID 25144892HCID 25144892, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of EXAMPLE 565B (62.8 mg), acrylic acid (9.91 μl) and 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate Methanaminium (HATU, 54.9 mg) in tetrahydrofuran (3 ml) was added triethylamine (36.6 μl). The reaction was stirred at room temperature overnight, diluted with ethyl acetate and washed with water. The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography, eluting with dichloromethane, to provide ethyl 3-(3-(6-acrylamidonaphthalen-1-yloxy)propyl)-7-o-tolyl-1H-indole-2-carboxylate. This ester was hydrolyzed with aqueous NaOH in tetrahydrofuran and methanol to provide the title compound. 1H NMR (500 MHz, methanol-d4) δ 8.22-8.25 (m, 2 H), 7.68 (dd, J=5.95, 3.20 Hz, 1 H), 7.59 (dd, J=9.15, 2.14 Hz, 1 H), 7.25-7.37 (m, 6 H), 7.05-7.08 (m, 2 H), 6.74 (dd, J=6.10, 2.44 Hz, 1 H), 6.46-6.55 (m, 1 H), 6.38-6.44 (m, 1 H), 5.80 (dd, J=10.07, 1.83 Hz, 1 H), 4.20 (t, J=5.95 Hz, 2 H), 3.40-3.56 (m, 2 H), 2.34 (t, J=6.71 Hz, 2 H), 2.11 (s, 3 H).

Sources & evidence

ORD record
ord-fbf644c4aa0d49449b872264b7849ef1
Source dataset
uspto-grants-2015_05
Patent number
US09035047B2

Reaction notes

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