Acetyl chloride → {1-[4-(2-Acetylamino-6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)-phenyl]-cyclobutyl}-carbamic Acid Tert-butyl Ester

HRID 2362174Notes

Reaction equation

HRID 2362174 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:22][N:21]4[N:30]=[C:31]([NH2:33])[N:32]=[C:20]4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:35](Cl)(=[O:37])[CH3:36]>CN(C1C=CN=CC=1)C.O1CCOCC1.C(Cl)Cl>[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:22][N:21]4[N:30]=[C:31]([NH:33][C:35](=[O:37])[CH3:36])[N:32]=[C:20]4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 6367Acetyl chlorideHCID 66823557HCID 66823557, compound

Product 1

HCID 66823339{1-[4-(2-Acetylamino-6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)-phenyl]-cyclobutyl}-carbamic Acid Tert-butyl EsterYield 58.3%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To the solution of 6-1 (100 mg, 0.22 mmol) and Et3 N (0.2 mL) DMAP (2 mg) in dioxane (2 mL) was added acetyl chloride (21 mg, 0.25 mmol) and the mixture was heated at 100° C. for 10 h. The mixture was diluted with 20 mL of DCM, the combined organic phase was washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep.TLC to give 64 mg of 6-3.

Workup

  1. washthe combined organic phase was washed with brine
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by prep.TLC

Sources & evidence

ORD record
ord-528453549bd54509bb67ee7f1a23d294
Source dataset
uspto-grants-2014_04
Patent number
US08691825B2

Reaction notes

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