Furan-3-boronic acid → HCID 11311785, compound

HRID 2106336Notes

Reaction equation

HRID 2106336 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:11](=[C:12](OS(C(F)(F)F)(=O)=O)[N:13]([CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[N:14]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[O:31]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32]1>>[CH:18]1([N:13]2[C:12]([C:33]3[CH:34]=[CH:35][O:31][CH:32]=3)=[C:11]3[C:15]([CH2:16][CH2:17][NH:8][CH2:9][CH2:10]3)=[N:14]2)[CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

3

Reactant 2

HCID 2734358Furan-3-boronic acidHCID 86598377HCID 86598377, compound

Product 1

HCID 11311785HCID 11311785, compoundYield 83.6%

Procedure

The title compound (101 mg) was prepared according to Example 180 using 202 mg of 2-cyclopentyl-3-trifluoromethanesulfonyloxy-4,5,7,8-tetrahydro-2H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester (Example 180, Step A) and 149 mg of 3-furanboronic acid. MS (ESI): exact mass calculated for C16H21N3O, 271.17; found, m/z 272.5 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.73-7.72 (m, 2H), 6.57-6.56 (m, 1H), 4.64 (m, 1H), 3.40-3.38 (m, 2H), 3.16-3.14 (m, 2H), 2.86-2.84 (m, 2H), 2.03-1.91 (m, 6H), 1.66-1.64 (m, 2H).

Sources & evidence

ORD record
ord-007019c0e2844e57b7f9401c3902a464
Source dataset
uspto-grants-2009_08
Patent number
US07579470B2

Reaction notes

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