3-Pyridinylboronic acid → HCID 118290329, compound

HRID 57144Notes

Reaction equation

HRID 57144 reaction equation
[N:1]1([CH2:5][CH2:6][N:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([CH:18]([CH3:20])[CH3:19])[CH:13]=3)[N:9]=[C:8]2[CH:21]2[CH2:26][CH2:25][N:24]([C:27]3[N:32]=[CH:31][N:30]=[C:29]([NH2:33])[C:28]=3Br)[CH2:23][CH2:22]2)[CH2:4][CH2:3][CH2:2]1.[N:35]1[CH:40]=[CH:39][CH:38]=[C:37](B(O)O)[CH:36]=1>>[N:1]1([CH2:5][CH2:6][N:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([CH:18]([CH3:20])[CH3:19])[CH:13]=3)[N:9]=[C:8]2[CH:21]2[CH2:26][CH2:25][N:24]([C:27]3[N:32]=[CH:31][N:30]=[C:29]([NH2:33])[C:28]=3[C:37]3[CH:36]=[N:35][CH:40]=[CH:39][CH:38]=3)[CH2:23][CH2:22]2)[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 894427436-{4-[1-(2-Azetidin-1-yl-ethyl)-4-(2-isopropyl-pyridin-4-yl)-1H-imidazol-2-yl]-piperidin-1-yl}-5-bromo-pyrimidin-4-ylamine

Product 1

HCID 118290329HCID 118290329, compound

Procedure

The title compound was prepared according to the procedure described for the preparation of compound “8” by using 6-{4-[1-(2-azetidin-1-yl-ethyl)-4-(2-isopropyl-pyridin-4-yl)-1H-imidazol-2-yl]-piperidin-1-yl}-5-bromo-pyrimidin-4-ylamine and 3-pyridinylboronic acid as the starting materials. LC-MS (M+H=524, obsd=524). 1H NMR (400 MHz, DMSO-d6) δ 8.59-8.50 (m, 2H), 8.38 (dd, J=5.1, 0.8 Hz, 1H), 8.11 (s, 1H), 7.80-7.72 (m, 2H), 7.53-7.47 (m, 2H), 7.43 (dd, J=5.1, 1.6 Hz, 1H), 5.92 (s, 2H), 3.85 (t, J=6.1 Hz, 2H), 3.40-3.27 (m, 5H), 3.63 (d, J=3.1 Hz, 1H), 3.12 (s, 5H), 3.01 (p, J=6.9 Hz, 1H), 2.85 (dt, J=10.1, 5.0 Hz, 1H), 2.77-2.63 (m, 4H), 2.01-1.87 (m, 2H), 1.65-1.52 (m, 4H), 1.25 (d, J=6.9 Hz, 6H).

Workup

  1. customdescribed for the preparation of compound “8”

Sources & evidence

ORD record
ord-eff4dbf18a0f499e9d9acac464205842
Source dataset
uspto-grants-2016_09
Patent number
US09434714B2

Reaction notes

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