Sodium hydride → 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-[2-(3,3-dimethylazetidin-2-one-1-yl)phenyl]piperidin-3-ol

HRID 1392390Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1([C:19]([NH:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[NH:34][C:35](=[O:42])[C:36]([CH3:41])([CH3:40])[CH:37](Cl)C)[CH2:24][CH:23]2[OH:43])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11].[H-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1([C:19]([NH:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[N:34]3[CH2:37][C:36]([CH3:41])([CH3:40])[C:35]3=[O:42])[CH2:24][CH:23]2[OH:43])=[O:20])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1)=[O:11]

Participants

Conditions

Temperature: 50 °C

Procedure

The solution of 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-[2-(3-chloro-2,2-dimethylbutyryl)aminophenyl]piperidin-3-ol (4.1 g) obtained in Step 3 in 50 ml of dimethylformamide was cooled to 0° C. Sodium hydride (NaH, 60%; 640 mg) was added to the reaction mixture, which was then stirred overnight at 50° C., diluted with ethyl acetate, washed with a brine, and then dried and concentrated on sodium sulfate. The resulting residue was purified with column chromatography to give 2.1 g of the titled compound.

Workup

washwashed with a brine
customdried
concentrationconcentrated on sodium sulfate
customThe resulting residue was purified with column chromatography

Sources & evidence

ORD record: ord-432ed7e5e9884d57a14f9aa2379af906
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07342027B2

Reaction notes

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