4-(Dimethylamino)phenylboronic acid → HCID 59752613, compound

HRID 749886Notes

Reaction equation

HRID 749886 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]([CH2:18][CH3:19])[N:14]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[CH3:28][N:29]([CH3:39])[C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1>>[CH2:18]([N:13]1[C:12]([C:33]2[CH:34]=[CH:35][C:30]([N:29]([CH3:39])[CH3:28])=[CH:31][CH:32]=2)=[C:11]2[C:15]([CH2:16][CH2:17][NH:8][CH2:9][CH2:10]2)=[N:14]1)[CH3:19]

Participants

3

Reactant 2

HCID 27343444-(Dimethylamino)phenylboronic acidHCID 86598381HCID 86598381, compound

Product 1

HCID 59752613HCID 59752613, compoundYield 40.4%

Procedure

The title compound (57 mg) was prepared according to Example 263 using 205 mg of 2-ethyl-3-trifluoromethanesulfonyloxy-4,5,7,8-tetrahydro-2H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester (Example 193, Step A) and 115 mg of 4-dimethylaminophenylboronic acid. MS (ESI): exact mass calculated for C17H24N4, 284.20; found, m/z 285.5 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.87-7.85 (m, 2H), 7.65-7.63 (m, 2H), 4.67 (br s, 2H), 4.06 (q, J=9.0 Hz, 2H), 4.00-3.62 (m, 2H), 3.36 (s, 6H), 3.32-3.29 (m, 2H), 3.18-2.81 (m, 2H), 1.31 (t, J=9.0 Hz, 3H).

Sources & evidence

ORD record
ord-8918891d3b4f497585a273c08bce83d3
Source dataset
uspto-grants-2008_07
Patent number
US07402680B2

Reaction notes

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