Potassium Carbonate → 1-(Cyclopropylmethyl)-4-({1-[(6-methylpyridin-3-yl)carbonyl]azetidin-3-yl}carbonyl)-1,4-diazepane

HRID 1402758Notes

Reaction equation

[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:13][CH:12]([C:14]([N:16]3[CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[O:15])[CH2:11]2)=[O:9])=[CH:4][CH:3]=1.Br[CH2:24][CH:25]1[CH2:27][CH2:26]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:25]1([CH2:24][N:19]2[CH2:20][CH2:21][CH2:22][N:16]([C:14]([CH:12]3[CH2:13][N:10]([C:8]([C:5]4[CH:6]=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=4)=[O:9])[CH2:11]3)=[O:15])[CH2:17][CH2:18]2)[CH2:27][CH2:26]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of 1-({1-[(6-methylpyridin-3-yl)carbonyl]azetidin-3-yl}carbonyl)-1,4-diazepane (100 mg, 0.33 mmol) and 1-(bromomethyl)cyclopropane (53 mg, 0.39 mmol) in ACN (5 mL) was added potassium carbonate (91 mg, 0.66 mmol). The mixture was heated to 70° C. in a sealed tube for 20 hours and then concentrated at reduced pressure. The crude residue was purified by silica FCC (eluting with 97:3:1 DCM/MeOH/NH3) and then preparative HPLC (Method 2) to give the title compound (45 mg, 38% yield) as pale yellow oil

Workup

concentrationconcentrated at reduced pressure
customThe crude residue was purified by silica FCC (eluting with 97:3:1 DCM/MeOH/NH3)

Sources & evidence

ORD record: ord-8af3eb96383e463db6968ffcdc68cc7f
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912176B2

Reaction notes

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