Propionyl bromide → HCID 9810305, compound

HRID 1198691Notes

Reaction equation

HRID 1198691 reaction equation
[C:1](Br)(=[O:4])[CH2:2][CH3:3].[NH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:47]([F:50])([F:49])[F:48])=[C:11]([N:13]2[C:17](=[O:18])[N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[S:32](=[O:42])(=[O:41])[NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[CH:22][CH:21]=3)[C:15]([CH2:43][CH2:44][CH2:45][CH3:46])=[N:14]2)[CH:12]=1>>[C:37]([O:36][C:34]([NH:33][S:32]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[C:23]1[CH:24]=[CH:25][C:20]([CH2:19][N:16]2[C:15]([CH2:43][CH2:44][CH2:45][CH3:46])=[N:14][N:13]([C:11]3[CH:12]=[C:7]([NH:6][C:1](=[O:4])[CH2:2][CH3:3])[CH:8]=[CH:9][C:10]=3[C:47]([F:49])([F:48])[F:50])[C:17]2=[O:18])=[CH:21][CH:22]=1)(=[O:41])=[O:42])=[O:35])([CH3:38])([CH3:39])[CH3:40]

Participants

3

Reactant 2

HCID 69018Propionyl bromideHCID 19102798HCID 19102798, compound

Product 1

HCID 9810305HCID 9810305, compoundYield 52%

Procedure

Propionyl bromide was reacted with 2-[5-amino-2-(trifluoromethyl)phenyl]-4-[[2'-[N-(t-butoxycarbonyl)sulfamoyl]biphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one (from Step F) according to the method of Example 26. Purification by silica gel flash chromatography (gradient elution with 0.5-5% MeOH in CH2Cl2) followed by semi-preparative HPLC (Zorbax C8 reverse phase column, elution with 60:40 and then 65:35 MeCN--H2O) gave 13 mg (52%) of the title compound as a solid, mp 158°-161° C.; homogeneous by TLC in 95:5 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 714 (M+2Li)+.

Workup

  1. customPurification
  2. washby silica gel flash chromatography (gradient elution with 0.5-5% MeOH in CH2Cl2)
  3. washZorbax C8 reverse phase column, elution with 60:40

Sources & evidence

ORD record
ord-b082df3b6fe247c7a30e3db5e2d027d7
Source dataset
uspto-grants-1994_01
Patent number
US05281614

Reaction notes

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