Sodium Hydroxide → HCID 25144892, compound

HRID 2199760Notes

Reaction equation

HRID 2199760 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-6f00840146964c3088ae97c245de95c6
Source dataset
uspto-grants-2016_06
Patent number
US09359296B2

Reaction notes

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