Triethylamine → HCID 66665523, compound

HRID 872317Notes

Reaction equation

HRID 872317 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]O)=[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.CS([Cl:47])(=O)=O>C(Cl)Cl>[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][Cl:47])=[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]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66665868HCID 66665868, compound

Product 1

HCID 66665523HCID 66665523, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

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) in DCM (1.9 mL), was treated with triethylamine (0.062 mL), cooled to 0° C. (ice bath), treated with methanesulfonyl chloride (0.028 mL, 0.358 mmol) and stirred for 2 hours at rt. The reaction mixture was partitioned between DCM and saturated aqueous sodium hydrogen-carbonate solution and the organic phase washed with brine, dried and concentrated in vacuo to give the crude title compound.

Workup

  1. customThe reaction mixture was partitioned between DCM and saturated aqueous sodium hydrogen-carbonate solution
  2. washthe organic phase washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-128bfc02f4b54e2b8c3fc3b38a76dd2e
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

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