Hydrochloric Acid → HCID 22241518, compound

HRID 892169Notes

Reaction equation

HRID 892169 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:21][C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]=3)[CH:15]=2)[C:3]=1[O:4][CH2:5][C:6]#N.C1COCC1.[OH-:37].[Na+].Cl.C[OH:41]>>[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:21][C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]=3)[CH:15]=2)[C:3]=1[O:4][CH2:5][C:6]([OH:41])=[O:37]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22241404HCID 22241404, compound

Product 1

HCID 22241518HCID 22241518, compound

Conditions

Temperature
60 °C

Procedure

To a solution of {2-methyl-6-[3-(quinolin-2-ylaminomethyl)-phenoxymethyl]-phenoxy}-acetonitrile (134 mg, 0.31 mmol, example 35a) in methanol (1 mL) is added THF (1 mL) followed by sodium hydroxide solution (0.2 mL, 10 N). The resulting mixture is warmed to 60° C. and stirred at this temperature for 3 h. The reaction mixture is then cooled to room temperature and acidified to ca. pH 5 with hydrochloric acid (1 mL, 2N), then extracted with ethyl acetate, washed with brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (silica, 10% methanol in dichloromethane) to give the title compound. 1H NMR (300 MHz, CDCl3) δ 8.10 (d, 1H), 7.80 (d, 1H), 7.68 (t, 2H), 7.40 (t, 1H), 7.25 (m, 2H), 7.04 (m, 3H), 6.90 (m, 3H), 6.6 (bs, 0.1H), 5.15 (s, 2H), 4.60 (d, 2H), 4.50 (s, 2H), 2.27 (s, 3H). MS (ESI) 429 (M+H)+.

Workup

  1. temperatureThe reaction mixture is then cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue is purified by flash chromatography (silica, 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-9580a5e6a6be423493f04cedaba96957
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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