Methanol → HCID 59180177, compound

HRID 601872Notes

Reaction equation

HRID 601872 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]([CH:23]=[CH:24][CH:25]=2)/[CH:10]=[C:11]2\[CH2:12][CH2:13][C:14]3[NH:15][C:16]([C:19]([O:21]C)=[O:20])=[CH:17][C:18]\2=3)[CH:2]=1.[OH-].[Li+].CO>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]([CH:23]=[CH:24][CH:25]=2)[CH2:10][CH:11]2[C:18]3[CH:17]=[C:16]([C:19]([OH:21])=[O:20])[NH:15][C:14]=3[CH2:13][CH2:12]2)[CH:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 66874088HCID 66874088, compound

Product 1

HCID 59180177HCID 59180177, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from (E)-methyl 4-(3-(pyridin-3-yl)benzylidene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.051 g, 0.15 mmol) and lithium hydroxide (0.067 g, 1.6 mmol in 1 mL water), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (2 mL) was used. The resulting product was purified by reverse phase HPLC, eluting with a gradient of 40-100% MeOH: water (with 0.1% formic acid) to afford the title compound. 15.0 mg, 31% yield. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.08-2.21 (m, 1H), 2.52-2.63 (m, 3H), 2.79-2.94 (m, 2H), 3.33-3.36 (m, 1H), 6.34 (s, 1H), 7.28 (d, J=7.57 Hz, 1H), 7.39-7.44 (m, 2H), 7.46-7.51 (m, 2H), 8.04 (dt, J=8.02, 1.90 Hz, 1H), 8.49 (dd, J=4.88, 1.46 Hz, 1H), 8.76 (d, J=2.00 Hz, 1H); LCMS-MS (ESI−) 317.2 (M−H); HPLC (UV=96.4%), (ELSD=100%).

Workup

  1. customThe resulting product was purified by reverse phase HPLC
  2. washeluting with a gradient of 40-100% MeOH

Sources & evidence

ORD record
ord-f0061848fb134e8998ffe29e21dfcaa2
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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