2,6-Dimethylbenzyl Chloride → HCID 59752647, compound

HRID 2106277Notes

Reaction equation

HRID 2106277 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[NH:14][N:13]=[C:12]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.[CH3:25][C:26]1[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[C:27]=1[CH2:28]Cl>>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([C:12]2[C:11]3[CH2:10][CH2:9][NH:8][CH2:17][CH2:16][C:15]=3[N:14]([CH2:28][C:27]3[C:30]([CH3:34])=[CH:31][CH:32]=[CH:33][C:26]=3[CH3:25])[N:13]=2)=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 2211542,6-Dimethylbenzyl ChlorideHCID 672690203-(4-chloro-phenyl)-4,5,7,8-tetrahydro-1H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester

Product 1

HCID 59752647HCID 59752647, compoundYield 24.6%

Procedure

The title compound (0.018 g) was prepared from 3-(4-chloro-phenyl)-4,5,7,8-tetrahydro-1H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester (Example 103, step B; 0.2 mmol) using 2,6-dimethylbenzyl chloride (0.3 mmol) in place of 2-chloromethyl-thiophene. MS (ESI): exact mass calculated for C22H24ClN3, 365.17; found, m/z 366.2 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.48-7.45 (m, 4H), 7.17-7.15 (br m, 1H), 7.11-7.09 (m, 2H), 5.51 (s, 2H), 3.43-3.41 (br m, 2H), 3.39-3.37 (br m, 2H), 3.31-3.29 (br m, 2H), 3.10-3.08 (br m, 2H), 2.31 (s, 3H).

Sources & evidence

ORD record
ord-03bcf47c4555430ba1ed2a6dab0c85cb
Source dataset
uspto-grants-2009_08
Patent number
US07579470B2

Reaction notes

Loading…