2-Methoxypyrimidine-5-boronic acid → HCID 178494067, compound

HRID 2103682Notes

Reaction equation

HRID 2103682 reaction equation
Br[C:2]1[CH:20]=[CH:19][C:5]2[N:6]=[C:7]([C@H:9]3[CH2:12][C@H:11]([N:13]4[CH2:17][CH2:16][CH2:15][C@H:14]4[CH3:18])[CH2:10]3)[S:8][C:4]=2[CH:3]=1.[CH3:21][O:22][C:23]1[N:28]=[CH:27][C:26](B(O)O)=[CH:25][N:24]=1.N1C=C(B(O)[OH:39])C=NC=1>>[CH3:21][O:22][C:23]1[N:28]=[CH:27][C:26]([C:2]2[CH:20]=[CH:19][C:5]3[N:6]=[C:7]([C@@H:9]4[CH2:12][C@H:11]([N:13]5[CH2:17][CH2:16][CH2:15][C@H:14]5[CH2:18][OH:39])[CH2:10]4)[S:8][C:4]=3[CH:3]=2)=[CH:25][N:24]=1

Participants

4

Reactant 3

HCID 27367782-Methoxypyrimidine-5-boronic acidHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 178461421HCID 178461421, compound

Product 1

HCID 178494067HCID 178494067, compound

Procedure

The title compound was prepared according to the procedure described in Example 1F, substituting the product of Example 36A for the product of Example 1E and substituting 2-methoxypyrimidine-5-boronic acid for pyrimidine-5-boronic acid. 1H NMR (400 MHz, CDCl3) δ ppm 8.77 (s, 2H) 8.06 (d, J=8.59 Hz, 1H) 7.98 (d, J=1.53 Hz, 1H) 7.59 (dd, J=8.59, 1.84 Hz, 1H) 4.08 (s, 3H) 3.55-3.68 (m, J=7.67 Hz, 2H) 3.36-3.47 (m, 1H) 3.25-3.35 (m, 1H) 3.03-3.14 (m, 1H) 2.72-2.87 (m, 2H) 2.61-2.72 (m, 1H) 2.40-2.54 (m, 3H) 1.87-2.01 (m, 1H) 1.69-1.85 (m, 2H) 1.51-1.70 (m, 1H). MS: (M+H)+=397.

Sources & evidence

ORD record
ord-c826f06088ad4fcb9e000a957dba1346
Source dataset
uspto-grants-2009_08
Patent number
US07576110B2

Reaction notes

Loading…