Propionyl bromide → HCID 19939418, compound

HRID 36276

Reaction equation

HRID 36276 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:46])=[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]=[C:25]([CH2:27][CH3:28])[CH:24]=[CH:23][C:22]=4[S:29](=[O:41])(=[O:40])[NH:30][C:31](=[O:39])[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=4[Cl:38])=[CH:17][CH:16]=3)[C:10]([CH2:42][CH2:43][CH2:44][CH3:45])=[N:9]2)[CH:7]=1.[C:47](Br)(=[O:50])[CH2:48][CH3:49]>CN(C1C=CN=CC=1)C>[CH2:42]([C:10]1[N:11]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[C:25]([CH2:27][CH3:28])[CH:24]=[CH:23][C:22]=3[S:29](=[O:40])(=[O:41])[NH:30][C:31](=[O:39])[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[Cl:38])=[CH:19][CH:20]=2)[C:12](=[O:13])[N:8]([C:6]2[CH:7]=[C:2]([NH:1][C:47](=[O:50])[CH2:48][CH3:49])[CH:3]=[CH:4][C:5]=2[Cl:46])[N:9]=1)[CH2:43][CH2:44][CH3:45]

Participants

4

Reactant 2

HCID 69018Propionyl bromideHCID 19939462HCID 19939462, compound

Product 1

HCID 19939418HCID 19939418, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

By the procedure of Example 69, 2-(5-amino-2-chlorophenyl)-5-n-butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]-5'-ethylbiphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (from Step D) was reacted with propionyl bromide in the presence of DMAP. Purification of the crude product by flash chromatography on silica gel (gradient elution with 1-4% MeOH in CH2Cl2) afforded a 65% yield of the title compound as a cream-colored solid, mp 144°-146° C.; homogeneous by TLC in 9:1 CH2Cl2 --MeOH; m/e 734 (M+1)+.

Workup

  1. customPurification of the crude product by flash chromatography on silica gel (gradient elution with 1-4% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-8e3ad536e2b044d0b3e1ff63c3a2902a
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Linked notes

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