2-Propanol, 2-methyl-, lithium salt (1:1) → N-(2-chlorobenzyl)-2-[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]-N-methylacetamide

HRID 505533Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:19]3[N:18]=[N:17][NH:16][C:15]=3[CH:14]=[CH:13][C:12]=2[Cl:20])[CH:9]=1)[C:5]#[N:6].CC(C)([O-])C.[Li+].Cl[CH2:28][C:29]([N:31]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[Cl:40])[CH3:32])=[O:30]>CN(C=O)C>[Cl:40][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[CH2:33][N:31]([CH3:32])[C:29](=[O:30])[CH2:28][N:16]1[C:15]2[CH:14]=[CH:13][C:12]([Cl:20])=[C:11]([O:10][C:8]3[CH:7]=[C:4]([C:5]#[N:6])[CH:3]=[C:2]([Cl:1])[CH:9]=3)[C:19]=2[N:18]=[N:17]1

Participants

Conditions

Temperature: 0 °C

Procedure

3-chloro-5-[(5-chloro-1H-1,2,3-benzotriazol-4-yl)oxy]benzonitrile (25 mg, 0.082 mmol) and lithium tert-butoxide (6.9 mg, 0.089 mmol) were dissolved in DMF (0.5 mL) and allowed to stir for 5 minutes. After this time, the reaction was cooled to 0° C. and 2-chloro-N-(2-chlorobenzyl)-N-methylacetamide as a solution in DMF (0.5 mL) was added dropwise. This was allowed to warm to room temperature and after 16 hours, the reaction was quenched with TFA, diluted with MeCN and purified by reverse phase chromatography eluting with 30-95% MeCN/H2O+0.1% TFA. Product fractions were lyophilized to yield the title compound. 1H NMR (DMSO-d6) δ 7.84 (m, 1H), 7.83 (d, J=9.0 Hz, 1H), 7.79 (d, J=9.0 Hz, 1H), 7.58 (m, 1H), 7.51 (m, 1H), 7.47 (m, 1H), 7.35 (m, 3H), 6.05 (s, 2H), 4.62 (s, 2H), 3.20 (s, 3H).

Workup

temperatureto warm to room temperature and after 16 hours
customthe reaction was quenched with TFA
additiondiluted with MeCN
custompurified by reverse phase chromatography
washeluting with 30-95% MeCN/H2O+0.1% TFA

Sources & evidence

ORD record: ord-6e690e0b429e42248c38c11e326c9add
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781454B2

Reaction notes

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