N-Methylethylamine → HCID 20792177, compound

HRID 2103126Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[O:13][C:12]2[CH:14]=[C:15]([F:21])[C:16]([C:18](O)=[O:19])=[CH:17][C:11]=2[O:10]1.[C:29](C1NC=CN=1)([C:31]1[NH:32][CH:33]=CN=1)=O.C(NC)C>CN(C)C=O>[CH2:31]([N:32]([CH3:33])[C:18]([C:16]1[C:15]([F:21])=[CH:14][C:12]2[O:13][C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[O:10][C:11]=2[CH:17]=1)=[O:19])[CH3:29]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of [2-(2,4-dichloro-phenyl)-6-fluoro-2-(4-fluoro-phenyl)-benzo[1,3]dioxole-5-carboxylic acid (Example 108d, 220 mg; 0.52 mmol; 1 eq.) in N,N-dimethylformamide (5 mL), was added carbonyl diimidazole (110 mg; 0.68 mmol; 1.3 eq.) and the mixture stirred 2 h at 20° C. A solution of ethyl-methylamine in N,N-dimethylformamide (1M, 1 mL; 1.3 mmol; 2.5 eq.) was added and the reaction mixture stirred 4 days at 20° C. Purification by preparative HPLC (YMC pro C18) afforded the title compound as 10 mM DMSO stock solution.

Workup

stirringthe reaction mixture stirred 4 days at 20° C
customPurification by preparative HPLC (YMC pro C18)

Sources & evidence

ORD record: ord-304681670a57485d9dd5230b528a365a
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576088B2

Reaction notes

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