1-Methyl-2-oxopyridine-3-boronic acid → 4-[3-(1-Methyl-2-oxo-1,2-dihydro-pyridin-3-yl)-pyrazolo[1,5-a]pyrimidin-5-yl]-piperazine-1-carboxylic acid isopropyl ester

HRID 1478269Notes

Reaction equation

HRID 1478269 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][N:16]3[N:19]=[CH:20][C:21](Br)=[C:15]3[N:14]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[CH3:23][N:24]1[CH:29]=[CH:28][CH:27]=[C:26](B(O)O)[C:25]1=[O:33]>>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][N:16]3[N:19]=[CH:20][C:21]([C:26]4[C:25](=[O:33])[N:24]([CH3:23])[CH:29]=[CH:28][CH:27]=4)=[C:15]3[N:14]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 748904041-Methyl-2-oxopyridine-3-boronic acidHCID 86697433Isopropyl 4-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carboxylate

Product 1

HCID 866974374-[3-(1-Methyl-2-oxo-1,2-dihydro-pyridin-3-yl)-pyrazolo[1,5-a]pyrimidin-5-yl]-piperazine-1-carboxylic acid isopropyl ester

Procedure

Prepared similarly to the preparation of example 5.6.9 from 4-(3-bromo-pyrazolo[1,5-a]pyrimidin-5-yl)-piperazine-1-carboxylic acid isopropyl ester and (1-methyl-2-oxo-1,2-dihydropyridin-3-yl)boronic acid to provide a yellow powder as a free base, mp. 206-207° C. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.23 (d, J=6.32 Hz, 6 H) 3.53 (s, 7 H) 3.70-3.82 (m, 4 H) 4.83 (spt, J=6.23 Hz, 1H) 6.37 (t, J=6.82 Hz, 1 H) 6.78 (d, J=7.83 Hz, 1 H) 7.55 (dd, J=6.57, 1.26 Hz, 1 H) 8.64 (dd, J=7.20, 1.14 Hz, 1 H) 8.72 (d, J=7.83 Hz, 1 H) 8.96 (s, 1 H). 13C NMR (100 MHz, DMSO-d6) δ ppm 21.97, 37.39, 42.84, 44.11, 68.16, 96.94, 100.56, 105.49, 122.80, 132.49, 135.00, 136.42, 144.40, 144.56, 154.29, 155.46, 160.29. LRMS (ESI) m/z 397.1 [(M+H)]+, calc'd for C20H24N6O3: 396.45.

Workup

  1. customto provide a yellow powder as a free base, mp. 206-207° C

Sources & evidence

ORD record
ord-7eacb62198d84137a9c4bdd56b8a3630
Source dataset
uspto-grants-2016_08
Patent number
US09403832B2

Reaction notes

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