{6-[(tert-Butoxycarbonyl)amino]pyridin-3-yl}boronic acid → HCID 86680679, compound

HRID 1615442Notes

Reaction equation

HRID 1615442 reaction equation
O(P(O[C:18]1[N:19]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:21][O:22][CH:23]=1)(OC1C=CC=CC=1)=O)C1C=CC=CC=1.[C:31]([O:35][C:36]([NH:38][C:39]1[N:44]=[CH:43][C:42](B(O)O)=[CH:41][CH:40]=1)=[O:37])([CH3:34])([CH3:33])[CH3:32]>>[C:31]([O:35][C:36]([NH:38][C:39]1[N:44]=[CH:43][C:42]([C:18]2[N:19]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:20][CH2:21][O:22][CH:23]=2)=[CH:41][CH:40]=1)=[O:37])([CH3:34])([CH3:32])[CH3:33]

Participants

3

Reactant 2

HCID 54751702{6-[(tert-Butoxycarbonyl)amino]pyridin-3-yl}boronic acidHCID 86680661tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate

Product 1

HCID 86680679HCID 86680679, compoundYield 26%

Procedure

This compound was prepared from tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate and 6-(tert-butoxycarbonylamino)pyridin-3-ylboronic acid using a procedure similar to that described in Example 2 (Steps 1-3a) above. The product was isolated as a white solid (26% yield); 1H-NMR (d6-DMSO) 1.10 (9H, s), 1.46 (9H, s), 3.69 (2H, t), 4.10 (2H, t), 6.43 (1H, s), 7.51-7.54 (1H, m), 7.73 (1H, m), 8.06 (1H, s), 9.75 (1H, s); 13C-NMR (d6-DMSO) 27.9, 28.3, 41.7, 66.8, 111.3, 132.3, 133.1, 135.0, 143.9; MS ES(+) 378.0 M++1); HRMS m/z calcd for C19H27N3O5+H+ 378.2029 [M+H+]. Found 378.2035. IR λmax=1699 cm−1.

Sources & evidence

ORD record
ord-7b31542fa4e54c0ea586ddc501ea4979
Source dataset
uspto-grants-2014_07
Patent number
US08765751B2

Reaction notes

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