1,2-Dichloroethane → HCID 51357515, compound

HRID 1623774Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:12]([CH:16]=2)[C:13](O)=[O:14])[CH2:4][CH2:3]1.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([NH2:31])[CH:26]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:9]=[CH:10][C:11]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:12]([CH:16]=2)[C:13]([NH:31][C:27]2[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=2)=[O:14])[CH2:6][CH2:7]1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of 5-(4-methyl-1-piperazinyl)-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 40; 50 mg, 0.15 mmol), 3-pyridinamine (14.42 mg, 0.15 mmol), EDC (29.4 mg, 0.15 mmol), HOBT (23.46 mg, 0.15 mmol) and triethylamine (0.02 ml, 0.15 mmol) dissolved in DMF (5 ml) was stirred for 3 h at 40° C. The mixture was then filtered and 10 ml water was added to the filtrate. The mixture was then extracted with ethyl acetate (30 ml) and concentrated. The residue was then purified by reverse phase HPLC using a gradient of acetonitrile and 0.1% aqueous ammonia as the eluent. Evaporation of the product-containing fractions gave the title compound as a white solid. 25 mg.

Workup

filtrationThe mixture was then filtered
addition10 ml water was added to the filtrate
extractionThe mixture was then extracted with ethyl acetate (30 ml)
concentrationconcentrated
customThe residue was then purified by reverse phase HPLC
customEvaporation of the product-containing fractions

Sources & evidence

ORD record: ord-fa8dfc467174440f91c297041a32898e
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778939B2

Reaction notes

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