Hydrochloric Acid → HCID 66819248, compound

HRID 1295109Notes

Reaction equation

HRID 1295109 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]([CH:21]1[CH2:23][CH:22]1[C:24]([O:26]CC)=[O:25])=[CH:15]2.[OH-].[Na+].Cl.[CH3:32]O>O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]([C@@H:21]1[CH2:32][C@H:23]1[CH2:22][C:24]([OH:26])=[O:25])=[CH:15]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 22570234HCID 22570234, compound

Product 1

HCID 66819248HCID 66819248, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 2-{5-[3-(2-pyridylamino)propoxy]indolyl}cyclopropanecarboxylate (0.38 g, 1.056 mmol), as prepared in the preceding step, was dissolved in 7.5 mL of methanol. A solution of NaOH (0.13 g, 3.18 mmol) in water (2.5 mL) was added and the reaction was stirred at ambient temperature overnight. The base was then neutralized with an aqueous solution of HCl (3.18 mmol), and the solvent was evaporated under vacuum. The crude product was chromatographed on silica gel to obtain the title compound (200 mg, 57%). 1H NMR (400 MHz, CDCl3) 5 1.66 (m, 2H), 2.00 (m, 1H), 2.16 (m, 2H), 3.58 (m, 2H), 3.72 (m, 1H), 4.12 (t, 2H, J=5.8 Hz), 6.31 (dd, 1H, J=0.7, 3.2 Hz), 6.77 (m, 1H,), 6.85 (dd, 1H, J=2.3, 8.8 Hz), 6.97 (d, 1H, J=9.0 Hz), 7.06 (d, 1H, J=2.3 Hz), 7.13 (d, 1H, J=3.2 Hz), 7.33 (d, 1H, J=8.8 Hz), 7.77 (m, 2H). Mass spectrum (LCMS, ESI pos.) Calcd. for C21H23N3O3 352.2 (M+H); Found: 352.2.

Workup

  1. customthe solvent was evaporated under vacuum
  2. customThe crude product was chromatographed on silica gel

Sources & evidence

ORD record
ord-732658de07164d44b4050ccc329bc54c
Source dataset
uspto-grants-2007_07
Patent number
US07241789B2

Reaction notes

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