Phenylboronic Acid → HCID 118290318, compound

HRID 57143Notes

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.[C:35]1(B(O)O)[CH:40]=[CH:39][CH:38]=[CH:37][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:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:23][CH2:22]2)[CH2:4][CH2:3][CH2:2]1

Participants

Reactant 2

HCID 66827Phenylboronic Acid

HCID 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 118290318HCID 118290318, 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 benzenboronic acid as the starting materials. LC-MS (M+H=523, obsd=523). 1H NMR (400 MHz, DMSO-d6) δ 8.37 (dd, J=5.1, 0.8 Hz, 1H), 8.08 (s, 1H), 7.76 (s, 1H), 7.54-7.46 (m, 3H), 7.43 (dd, J=5.1, 1.6 Hz, 1H), 7.36 (dddd, J=9.9, 6.5, 2.9, 1.6 Hz, 3H), 5.65 (s, 2H), 3.83 (t, J=6.2 Hz, 2H), 3.79-3.66 (m, 2H), 3.09 (t, J=7.0 Hz, 4H), 3.00 (h, J=6.9 Hz, 1H), 2.92-2.79 (m, 1H), 2.69 (dd, J=20.7, 7.0 Hz, 1H), 1.92 (p, J=7.0 Hz, 2H), 1.59 (dt, J=8.0, 4.5 Hz, 4H), 1.25 (d, J=6.9 Hz, 6H).

Workup

customdescribed for the preparation of compound “8”

Sources & evidence

ORD record: ord-acfa05c72d2a48ed8b4df60ecc62d94a
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434714B2

Reaction notes

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