Sodium Carbonate → HCID 46852751, compound

HRID 1402743Notes

Reaction equation

HRID 1402743 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]([N:7]2[CH2:13][CH2:12][CH2:11][N:10]([CH:14]3[CH2:17][CH2:16][CH2:15]3)[CH2:9][CH2:8]2)=[O:6])[CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].[C:24](Cl)(=[O:27])[CH2:25][CH3:26]>ClCCl>[CH:14]1([N:10]2[CH2:11][CH2:12][CH2:13][N:7]([C:5]([CH:3]3[CH2:2][N:1]([C:24](=[O:27])[CH2:25][CH3:26])[CH2:4]3)=[O:6])[CH2:8][CH2:9]2)[CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 62324Propionyl chlorideHCID 667393581-(Azetidin-3-ylcarbonyl)-4-cyclobutyl-1,4-diazepane

Product 1

HCID 46852751HCID 46852751, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(azetidin-3-ylcarbonyl)-4-cyclobutyl-1,4-diazepane (125 mg, 0.53 mmol) in dichloromethane (5 ml) at 0° C. was added sodium carbonate (167 mg, 1.58 mmol) and propionyl chloride (58 mg, 0.63 mmol). The resulting mixture was stirred at RT for 13 h before volatiles were removed under reduced pressure. Purification by silica FCC (using a gradient of eluents; 100:0 to 98:2 DCM:2M NH3 in MeOH) followed by purification by preparative HPLC (Method 2) gave the title compound (18 mg, 12% yield) as pale yellow oil. LCMS data: Calculated MH1(294). Found 86% (MH1) m/z 294, Rt=3.18 min (Method D).

Workup

  1. customwere removed under reduced pressure
  2. customPurification by silica FCC (
  3. custom100:0 to 98:2 DCM:2M NH3 in MeOH) followed by purification by preparative HPLC (Method 2)

Sources & evidence

ORD record
ord-6cf759ea64e74ee48ce8f8e4074f8e9a
Source dataset
uspto-grants-2014_12
Patent number
US08912176B2

Reaction notes

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