(4-Methoxy-2-methylphenyl)boronic acid → benzyl (3R,4S)-3-{[3,6-diethyl-5-(4-methoxy-2-methylphenyl)pyrazin-2-yl]amino}-4-ethoxypyrrolidine-1-carboxylate

HRID 1297285Notes

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][C:41]1[CH:46]=[C:45]([O:47][CH3:48])[CH:44]=[CH:43][C:42]=1B(O)O>>[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:42]2[CH:43]=[CH:44][C:45]([O:47][CH3:48])=[CH:46][C:41]=2[CH3:40])[N:10]=1)[CH3:37]

Participants

Reactant 2

HCID 2773486(4-Methoxy-2-methylphenyl)boronic acid

HCID 58914572HCID 58914572, compound

Product 1

HCID 58914570benzyl (3R,4S)-3-{[3,6-diethyl-5-(4-methoxy-2-methylphenyl)pyrazin-2-yl]amino}-4-ethoxypyrrolidine-1-carboxylate

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 and but substituting 2-methyl-4-methoxy-phenyl boronic acid provided the title compound as an amorphous solid. 1H NMR (CDCl3) δ 1.04, 1.21, 2.04, 2.40, 2.65, 3.22˜3.26, 3.41, 3.52˜3.68, 3.75, 3.94, 4.03, 4.68, 5.08, 6.70, 6.74, 7.02, 7.28˜7.32; IR (liq.) 2971 (s), 2339 (w), 2166 (w), 2082 (w), 1957 (w), 1708 (s), 1564 (s), 1482 (s), 1420 (s), 1395 (s), 1349 (s), 1242 (s), 1169 (s), 1125 (s), 1096 (s) cm−1 HRMS (ESI) calcd for C30H38N4O4+H1 519.2971. found 519.2974.

Sources & evidence

ORD record: ord-596bcdbb173c461aa7b308ea79c18323
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250418B2

Reaction notes

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