Hydrochloric Acid → {4-[({4-[(4-Butylphenyl)ethynyl]benzyl}{[(4-cyanophenyl)amino]-carbonyl}amino)methyl]phenoxy}acetic acid

HRID 551907

Reaction equation

HRID 551907 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:44]=[CH:43][C:16]([CH2:17][N:18]([CH2:30][C:31]3[CH:42]=[CH:41][C:34]([O:35][CH2:36][C:37]([O:39]C)=[O:38])=[CH:33][CH:32]=3)[C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=3)=[O:20])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].Cl>CO.C1COCC1>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:44]=[CH:43][C:16]([CH2:17][N:18]([CH2:30][C:31]3[CH:42]=[CH:41][C:34]([O:35][CH2:36][C:37]([OH:39])=[O:38])=[CH:33][CH:32]=3)[C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=3)=[O:20])=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11621237Methyl [4-({{4-[(4-butylphenyl)ethynyl]benzyl}[(4-cyanoanilino)-carbonyl]amino}methyl)phenoxy]acetate

Product 1

HCID 11692676{4-[({4-[(4-Butylphenyl)ethynyl]benzyl}{[(4-cyanophenyl)amino]-carbonyl}amino)methyl]phenoxy}acetic acidYield 75.7%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl [4-({{4-[(4-butylphenyl)ethynyl]benzyl}[(4-cyanoanilino)-carbonyl]amino}methyl)phenoxy]acetate (65 mg) in MeOH/THF (2 ml, (1/1)) was added an aqueous solution of NaOH (2 mL, 1N). The reaction mixture was stirred at rt for 3 hrs. Then an aqueous solution of HCl (7 mL, 1N) was added and extracted with. Et2O (2×7 mL). The combined organic layers were dried over Na2SO4 and the solvents were removed under reduced pressure to give 48 mg of the title compound as a yellow powder. HPLC, Rt: 5.2 min (purity: 75.0%). LC/MS, M+(ESI): 572.4, M−(ESI): 570.4. 1H NMR (DMSO-d6) δ: 7.70 (m, 5H), 7.51 (d, J=7.9 Hz, 2H), 7.44 (d, J=7.9 Hz, 2H), 7.28-7.16 (m, 6h), 6.89 (d, J=8.7 Hz, 2H), 4.64 (s, 2H), 4.56 (s, 2H), 4.51 (s, 2H), 2.60 (t, J=7.7 Hz, 2H), 1.55 (m, 2H), 1.28 (m, 2H), 0.89 (t, J=7.2 Hz, 3H).

Workup

  1. extractionextracted with
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-d6566beec53f44b9b221b7baa8ceddc7
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Linked notes

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