Azetidine → HCID 86721448, compound

HRID 869597Notes

Reaction equation

HRID 869597 reaction equation
Cl[C:2]1[C:7]([CH2:8][C:9]2[CH:28]=[CH:27][C:12]3/[C:13](=[C:23](/[CH3:26])\[C:24]#[N:25])/[C:14]4[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:15]=4[O:16][CH2:17][C:11]=3[CH:10]=2)=[C:6]([CH2:29][CH2:30][CH3:31])[N:5]=[C:4]([CH3:32])[N:3]=1.[NH:33]1[CH2:36][CH2:35][CH2:34]1>C(O)C>[N:33]1([C:2]2[C:7]([CH2:8][C:9]3[CH:28]=[CH:27][C:12]4/[C:13](=[C:23](/[CH3:26])\[C:24]#[N:25])/[C:14]5[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:15]=5[O:16][CH2:17][C:11]=4[CH:10]=3)=[C:6]([CH2:29][CH2:30][CH3:31])[N:5]=[C:4]([CH3:32])[N:3]=2)[CH2:36][CH2:35][CH2:34]1

Participants

4

Reactant 2

HCID 10422AzetidineHCID 86721447HCID 86721447, compound

Product 1

HCID 86721448HCID 86721448, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

[step 4] (E)-2-{8-[(4-chloro-2-methyl-6-propylpyrimidin-5-yl)methyl]-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrile (140 mg, 3.13 mmol) obtained in step 3 was dissolved in ethanol (3 mL), azetidine (0.148 mL, 2.19 mmol) was added, and the mixture was stirred with heating at 50° C. for 2 hr. The mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2 v/v) to give the title compound (145 mg, 99%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2 v/v)

Sources & evidence

ORD record
ord-f9ace674d4c549528a3ef8aafc2f543d
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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