Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → (1-{4-[3-(1-Methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3-oxo-1-o-tolyl-propyl]-benzoyl}-piperidin-4-yl)-acetic acid ethyl ester

HRID 1617711Notes

Reaction equation

HRID 1617711 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[CH:5][C:4]([C:9](=[O:28])[CH2:10][CH:11]([C:19]2[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])=[CH:3]1.[CH2:29]([O:31][C:32](=[O:40])[CH2:33][CH:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)[CH3:30].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>O1CCCC1>[CH2:29]([O:31][C:32](=[O:40])[CH2:33][CH:34]1[CH2:39][CH2:38][N:37]([C:23](=[O:24])[C:22]2[CH:26]=[CH:27][C:19]([CH:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])[CH2:10][C:9]([C:4]3[CH:5]=[CH:6][C:7](=[O:8])[N:2]([CH3:1])[CH:3]=3)=[O:28])=[CH:20][CH:21]=2)[CH2:36][CH2:35]1)[CH3:30]

Participants

5

Reactant 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2760465Ethyl 2-(piperidin-4-yl)acetateHCID 670155254-[3-(1-Methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3-oxo-1-o-tolyl-propyl]-benzoic acid

Product 1

HCID 67015660(1-{4-[3-(1-Methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3-oxo-1-o-tolyl-propyl]-benzoyl}-piperidin-4-yl)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In analogy to example 207, step 2, 4-[3-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3-oxo-1-o-tolyl-propyl]-benzoic acid (example 207, step 1) was coupled with 2-(piperidin-4-yl)-acetic acid ethyl ester using BOP reagent in tetrahydrofuran to give the title compound as a light brown foam, MS (ESI+): m/z=529.3 [M+H]+.

Sources & evidence

ORD record
ord-d6e1efd2c9554fdc9498a23cfc8cf9f5
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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