Triethylamine → HCID 86691040, compound

HRID 872316Notes

Reaction equation

HRID 872316 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[C:20]4[CH:25]=[CH:24][C:23]([CH2:26][OH:27])=[CH:22][N:21]4[C:28]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C>C(Cl)Cl.CS(C)=O>[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[N:19]=[C:20]4[CH:25]=[CH:24][C:23]([CH:26]=[O:27])=[CH:22][N:21]4[C:28]=3[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[CH:16][CH:17]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 66665868HCID 66665868, compound

Product 1

HCID 86691040HCID 86691040, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of {1-[4-(6-hydroxymethyl-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (200 mg) and triethylamine (0.125 mL) in DCM (1.9 mL) at 0° C. was treated with a solution of pyridine-sulfur trioxide complex (142 mg, 0.894 mmol) in DMSO (0.021 mL). The reaction mixture was warmed to rt and stirred for 2 hours. The mixture was partitioned between ethyl acetate and water and the organic phase washed with water, dried and concentrated in vacuo to give the crude title compound which was used in the next step without further purification.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washthe organic phase washed with water
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b75bd7f18e3d4d14b8421834ade69596
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

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