Ethanol → HCID 69548455, compound

HRID 1936155Notes

Reaction equation

[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11]C(C#CC3C=CC(CC(OC)=O)=CC=3)=C[C:8]=2C)[CH:5]=[CH:4][N:3]=[CH:2]1.C([C:29]1[CH:34]=[CH:33][C:32]([C:35]2(NCCC)[CH2:37][CH2:36]2)=[CH:31][CH:30]=1)#C.O1CC[CH2:44][CH2:43]1.[OH-:47].[Na+].[CH2:49]([OH:51])[CH3:50]>>[N:1]1([C:6]2[CH:44]=[CH:43][C:36]([C:37]#[C:35][C:32]3[CH:31]=[CH:30][C:29]([CH2:50][C:49]([OH:47])=[O:51])=[CH:34][CH:33]=3)=[C:12]([CH3:11])[C:7]=2[CH3:8])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

Reactant 5

HCID 702Ethanol

HCID 8028Tetrahydrofuran

HCID 14798Sodium Hydroxide

HCID 22568926[1-(4-Ethynylphenyl)-cyclopropyl]-propylamine

HCID 86758076HCID 86758076, compound

Product 1

HCID 69548455HCID 69548455, compoundYield 70%

Procedure

Using General Procedure I; a solution of methyl [4-(4-imidazol-1ylmethyl-3-methyl-phenylethynyl)-phenyl]-acetate. (Compound 120, 45.0 mg, 0.13 mmol) in ethanol (2 mL) and tetrahydrofuran (2 mL) was treated with NaOH (80.0 mg, 2.0 mmols, 2.0 mL of a 1N aqueous solution) and stirred overnight at room temperature. Work-up afforded 30.0 mg (70%) of the title compound as a pale-orange solid.

Sources & evidence

ORD record: ord-2197472ce59d4da688b872f7a5d4a744
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06387951B1

Reaction notes

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