2-Methyl-6-methoxypyridine-3-boronic acid → HCID 58914559, compound

HRID 1297284Notes

Reaction equation

HRID 1297284 reaction equation
CN(C)C1N=CC([C:9]2[N:10]=[C:11]([CH2:36][CH3:37])[C:12]([NH:17][C@H:18]3[C@@H:22]([O:23][CH2:24][CH3:25])[CH2:21][N:20]([C:26]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:27])[CH2:19]3)=[N:13][C:14]=2[CH2:15][CH3:16])=C(C)C=1.[CH3:40][O:41][C:42]1[N:47]=[C:46]([CH3:48])[C:45](B(O)O)=[CH:44][CH:43]=1>>[CH2:36]([C:11]1[C:12]([NH:17][C@H:18]2[C@@H:22]([O:23][CH2:24][CH3:25])[CH2:21][N:20]([C:26]([O:28][CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[O:27])[CH2:19]2)=[N:13][C:14]([CH2:15][CH3:16])=[C:9]([C:45]2[C:46]([CH3:48])=[N:47][C:42]([O:41][CH3:40])=[CH:43][CH:44]=2)[N:10]=1)[CH3:37]

Participants

3

Reactant 2

HCID 27630842-Methyl-6-methoxypyridine-3-boronic acidHCID 58914572HCID 58914572, compound

Product 1

HCID 58914559HCID 58914559, compound

Procedure

Following the procedure for the preparation of benzyl (3R,4S)-3-({5-[6-(dimethylamino)-4-methylpyridin-3-yl]-3,6-diethylpyrazin-2-yl}amino)-4-ethoxypyrrolidine-1-carboxylate but substituting 6-methoxy-2-methylpyridin-3-ylboronic acid provided the title compound as an oil: 1H NMR (400 MHz, CDCl3) δ) 7.41–7.36, 6.64, 5.17–5.15, 4.78, 4.11, 4.02–3.97, 3.73–3.35, 2.70, 2.46, 2.28, 1.32–1.21, 1.13; IR (liq.) 2236 (w), 2018 (w), 1949 (w), 1709 (s), 1596, 1565, 1499, 1474 (s), 1420 (s), 1396, 1360, 1350, 1304 (s), 1126, 1097 cm−1 HRMS (ESI) calcd for C29H37N5O4+H1 520.2924. found 520.2924.

Sources & evidence

ORD record
ord-f50f25a20fc442c88267774809a1d936
Source dataset
uspto-grants-2007_07
Patent number
US07250418B2

Reaction notes

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