Diisopropylethylamine → HCID 44463034, compound

HRID 1881691Notes

Reaction equation

O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C.[F:21][C:22]([F:45])([F:44])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29]([N:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH:33]1[CH2:38][CH2:39][CH2:40][C:41](O)=[O:42])(=[O:31])=[O:30].Cl.CN(C)CCCN=C=NCC.Cl.Cl.[N:60]1([CH2:65][CH2:66][O:67][C:68]2([C:74]3[CH:75]=[N:76][CH:77]=[CH:78][CH:79]=3)[CH2:73][CH2:72][NH:71][CH2:70][CH2:69]2)[CH2:64][CH2:63][CH2:62][CH2:61]1>C(Cl)Cl>[N:76]1[CH:77]=[CH:78][CH:79]=[C:74]([C:68]2([O:67][CH2:66][CH2:65][N:60]3[CH2:64][CH2:63][CH2:62][CH2:61]3)[CH2:73][CH2:72][N:71]([C:41](=[O:42])[CH2:40][CH2:39][CH2:38][CH:33]3[CH2:34][CH2:35][CH2:36][CH2:37][N:32]3[S:29]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[C:22]([F:21])([F:45])[F:44])(=[O:30])=[O:31])[CH2:70][CH2:69]2)[CH:75]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1-Hydroxybenzotriazole hydrate (HOBT) (0.021 g, 0.158 mmol, 0.3 eq.) and N-ethyl-diisopropylamine (0.269 ml, 1.59 mmol, 3 eq.) were added to a solution of 4-(1-(2-(trifluoromethyl)phenylsulfonyl)piperidin-2-yl)butanoic acid (0.251 g, 0.66 mmol, 1.25 eq.) in methylene chloride (7 ml). The mixture was cooled to 0° C., 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCl) (0.152 g, 0.792 mmol, 1.5 eq.) was added and the mixture was stirred for approx. 15 min. 3-(4-(2-(Pyrrolidin-1-yl)ethoxy)piperidin-4-yl)pyridine dihydrochloride (0.184 g, 0.528 mmol, 1 eq.) was then added. The reaction mixture was stirred at room temperature for 72 h.

Workup

stirringThe reaction mixture was stirred at room temperature for 72 h.

Sources & evidence

ORD record: ord-fb17160bc5fb4b079a1611500a3ba07a
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318769B2

Reaction notes

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