2-(Prop-2-ynyloxy)ethyl acetate → Acetic acid 2-[3-(2-{2-[(pyridin-4-ylmethyl)-amino]-benzoylaminooxymethyl}-phenyl)-prop-2-ynyloxy]-ethyl ester

HRID 1663133Notes

Reaction equation

HRID 1663133 reaction equation
I[C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][O:5][NH:6][C:7](=[O:22])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][CH2:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1.[C:27]([O:30][CH2:31][CH2:32][O:33][CH2:34][C:35]#[CH:36])(=[O:29])[CH3:28]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[N:19]1[CH:20]=[CH:21][C:16]([CH2:15][NH:14][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C:7]([NH:6][O:5][CH2:4][C:3]2[CH:23]=[CH:24][CH:25]=[CH:26][C:2]=2[C:36]#[C:35][CH2:34][O:33][CH2:32][CH2:31][O:30][C:27](=[O:29])[CH3:28])=[O:22])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 27801402-(Prop-2-ynyloxy)ethyl acetateHCID 11487973N-((2-iodobenzyl)oxy)-2-((pyridin-4-ylmethyl)amino)benzamide

Product 1

HCID 11317445Acetic acid 2-[3-(2-{2-[(pyridin-4-ylmethyl)-amino]-benzoylaminooxymethyl}-phenyl)-prop-2-ynyloxy]-ethyl ester

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

The same procedure was used as described for the preparation of example 365, but without addition of tetrabutylammonium iodide. Starting materials: N-(2-Iodo-benzyloxy)-2-[(pyridin-4-ylmethyl)-amino]-benzamide (see example 360) and 2-(prop-2-ynyloxy)ethyl acetate (Maybridge).

Workup

  1. customas described for the preparation of example 365

Sources & evidence

ORD record
ord-40ccea6139eb4fa291587f29ff377a17
Source dataset
uspto-grants-2011_10
Patent number
US08034811B2

Reaction notes

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