Cyclopropanecarbonyl chloride → HCID 54335986, compound

HRID 1839192Notes

Reaction equation

HRID 1839192 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][NH:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH:22]1([C:25](Cl)=[O:26])[CH2:24][CH2:23]1>C(Cl)Cl>[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][N:15]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[C:25]([CH:22]2[CH2:24][CH2:23]2)=[O:26])[CH2:9]1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 21904427HCID 21904427, compound

Product 1

HCID 54335986HCID 54335986, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(1-Boc-piperidin-3-ylmethyl)-N-(pyridin-3-yl)amine 17 (56 mg, 0.19 mmol) and piperidinomethyl polystyrene resin (3.5 mM/g, 60 mg) in 0.6 mL of dry CH2Cl2 was added cyclopropanecarbonyl chloride (98%, 21 μL, 1.2 eq.) at room temperature. After being shaken at room temperature overnight, the reaction mixture was passed through an aminopropyl NH2 cartridge and washed with CH2Cl2. Removal of CH2Cl2 afforded Cyclopropanecarboxylic acid N-(1-Boc-piperidin-3-ylmethyl)-N-(pyridin-3-yl)amide 22 (50 mg, 73%). LRMS 260 (M−100)+.

Workup

  1. washwashed with CH2Cl2
  2. customRemoval of CH2Cl2

Sources & evidence

ORD record
ord-a2a469335b534e03bc1133213d59abde
Source dataset
uspto-grants-2004_01
Patent number
US06677332B1

Reaction notes

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