Azetidine → HCID 67028622, compound

HRID 2066149Notes

Reaction equation

HRID 2066149 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]([N:11]2[CH2:16][CH2:15][N:14]([S:17]([C:20]3[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][C:21]=3[CH3:28])(=[O:19])=[O:18])[CH2:13][C@@H:12]2[CH3:29])=[O:10])=[CH:4][CH:3]=1.[NH:30]1[CH2:33][CH2:32][CH2:31]1>C(O)(C)C>[ClH:1].[N:30]1([C:2]2[N:7]=[C:6]([CH3:8])[C:5]([C:9]([N:11]3[CH2:16][CH2:15][N:14]([S:17]([C:20]4[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][C:21]=4[CH3:28])(=[O:19])=[O:18])[CH2:13][C@@H:12]3[CH3:29])=[O:10])=[CH:4][CH:3]=2)[CH2:33][CH2:32][CH2:31]1

Participants

4

Reactant 2

HCID 10422AzetidineHCID 591613924-({(3S)-4-[(6-Chloro-2-methyl-3-pyridinyl)carbonyl]-3-methyl-1-piperazinyl}sulfonyl)-3-methylbenzonitrile

Product 1

HCID 67028622HCID 67028622, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
120 °C

Procedure

4-({(3S)-4-[(6-Chloro-2-methyl-3-pyridinyl)carbonyl]-3-methyl-1-piperazinyl}sulfonyl)-3-methylbenzonitrile (may be prepared as described in Example 25) (65 mg, 0.15 mmol) was weighed into a microwave vial and suspended in isopropanol (1.5 ml). Azetidine (0.203 ml, 3.01 mmol) was added and the mixture was heated in the microwave to 120° C. for 18 h with stirring. LCMS analysis showed >80% conversion. The reaction mixture was concentrated to give the crude material as a colourless gum (273 mg). This was purified by MDAP to give the free base of the title compound as a colourless gum (32 mg).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give the crude material as a colourless gum (273 mg)
  3. customThis was purified by MDAP

Sources & evidence

ORD record
ord-22e7d64208c54f38bcc59b44fcc09728
Source dataset
uspto-grants-2012_10
Patent number
US08288388B2

Reaction notes

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