trans-2-Phenyl-1-cyclopropanecarbonyl chloride → HCID 25196568, compound

HRID 572007Notes

Reaction equation

HRID 572007 reaction equation
[C:1]1([C@@H:7]2[CH2:9][C@H:8]2[C:10](Cl)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Cl.[CH:15]1([N:19]2[CH2:25][CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH2:18][CH2:17][CH2:16]1>>[CH:15]1([N:19]2[CH2:25][CH2:24][CH2:23][N:22]([C:10]([C@@H:8]3[CH2:9][C@H:7]3[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[O:11])[CH2:21][CH2:20]2)[CH2:18][CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 13656trans-2-Phenyl-1-cyclopropanecarbonyl chlorideHCID 574239521-Cyclobutyl-1,4-diazepane dihydrochloride

Product 1

HCID 25196568HCID 25196568, compound

Procedure

This example was prepared according to Example 4 utilizing trans-2-phenyl-1-cyclopropanecarbonyl chloride and 1-N-cyclobutyl-1,4-diazepane dihydrochloride, which was prepared according to Zaragoza, et. al. J. Med. Chem. 2004, 47, 2833-2838. m/z (ES+) M+1=299.2; HPLC tR=1.62 min. 1H NMR (500 MHz, CDCl3) δ 7.26 (t, J=7.6 Hz, 2H), 7.20-7.15 (m, 1H), 7.13-7.08 (m, 2H), 3.73-3.59 (m, 4H), 2.92-2.83 (m, 1H), 2.54-2.36 (m, 5H), 2.08-1.98 (m, 2H), 1.97-1.90 (m, 1H), 1.89-1.74 (m, 4H), 1.66 (ddd, J=9.2, 5.3, 4.1 Hz, 2H), 1.63-1.55 (m, 1H), 1.25 (m, 1H).

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-391d3df6986d46958f32b71ea8dda316
Source dataset
uspto-grants-2015_05
Patent number
US09029381B2

Reaction notes

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