Morpholine → HCID 58011820, compound

HRID 660950Notes

Reaction equation

HRID 660950 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH:14]=O)[C:11](=[O:16])[N:10]([CH2:17][C:18]([NH:20][C:21]([CH3:33])([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[CH3:22])=[O:19])[N:9]=2)=[CH:4][CH:3]=1.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCl.CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH2:14][N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[C:11](=[O:16])[N:10]([CH2:17][C:18]([NH:20][C:21]([CH3:22])([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:30])([F:31])[F:32])[CH:24]=3)[CH3:33])=[O:19])[N:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 58011768HCID 58011768, compound

Product 1

HCID 58011820HCID 58011820, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

0.10 g (0.21 mmol) of 2-[3-(4-chlorophenyl)-4-(2-oxoethyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-{1-methyl-1-[3-(trifluoromethyl)phenyl]ethyl}-acetamide from Example 401 are dissolved in 30 ml of dichloromethane and 0.4 ml of DMF and stirred with 22 mg (0.2 mmol) of morpholine for 1 hr at RT. Next, 66 mg (0.31 mmol) of sodium triacetoxyborohydride are added and the mixture is stirred for 18 hrs at RT. The reaction mixture is treated with 10 ml of saturated sodium hydrogen carbonate solution and extracted three times with 10 ml ethyl acetate each time. The combined organic phases are dried over sodium sulphate, filtered and concentrated in vacuo. The crude product is purified by preparative HPLC [Method 10]. 11.0 mg (10% of theory) of the target compound are obtained.

Workup

  1. extractionextracted three times with 10 ml ethyl acetate each time
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by preparative HPLC [Method 10]
  6. custom11.0 mg (10% of theory) of the target compound are obtained

Sources & evidence

ORD record
ord-db6b7299f56e486897d6eb43883eb001
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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