Valeryl chloride → HCID 10349732, compound

HRID 1198682Notes

Reaction equation

HRID 1198682 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:42])=[C:6]([N:8]2[C:12](=[O:13])[N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[S:27](=[O:37])(=[O:36])[NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:17][CH:16]=3)[C:10]([CH2:38][CH2:39][CH2:40][CH3:41])=[N:9]2)[CH:7]=1.[C:43](Cl)(=[O:48])[CH2:44][CH2:45][CH2:46][CH3:47]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:32]([O:31][C:29]([NH:28][S:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:18]1[CH:17]=[CH:16][C:15]([CH2:14][N:11]2[C:10]([CH2:38][CH2:39][CH2:40][CH3:41])=[N:9][N:8]([C:6]3[CH:7]=[C:2]([NH:1][C:43](=[O:48])[CH2:44][CH2:45][CH2:46][CH3:47])[CH:3]=[CH:4][C:5]=3[Cl:42])[C:12]2=[O:13])=[CH:20][CH:19]=1)(=[O:37])=[O:36])=[O:30])([CH3:34])([CH3:35])[CH3:33]

Participants

5

Reactant 2

HCID 61186Valeryl chlorideHCID 10077491HCID 10077491, compound

Product 1

HCID 10349732HCID 10349732, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of 78 mg (0.128 mmol) of 2-(5-amino-2-chlorophenyl)-4-[[2'-[N-(t-butoxycarbonyl)sulfamoyl]biphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one (from Example 25), 76 μL (77 mg, 0.64 mmol) of valeryl chloride, and 15.6 mg (0.128 mmol) of 4-(dimethylamino)pyridine (DMAP) in 1 mL of dry pyridine was stirred overnight at room temperature. The mixture was quenched by addition of water and extracted twice with ethyl acetate. The combined organic fractions were washed twice with water, then with brine, and dried over Na2SO4. The filtered solution was concentrated, and the residue was flash chromatographed twice on silica gel (gradient elution with 0.5-3% methanol in CH2Cl2) to provide 41 mg (46%) of the title compound as a white solid, mp 177°-179° C.; homogeneous by TLC (9:1 CH2Cl2 --MeOH).

Workup

  1. customThe mixture was quenched by addition of water
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic fractions were washed twice with water
  4. dry with materialwith brine, and dried over Na2SO4
  5. concentrationThe filtered solution was concentrated
  6. customchromatographed twice on silica gel (gradient elution with 0.5-3% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-e77cd2b7adaa41368c0da5cd4f6aaefc
Source dataset
uspto-grants-1994_01
Patent number
US05281614

Reaction notes

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