Bromide ion → HCID 57407244, compound

HRID 623670Notes

Reaction equation

HRID 623670 reaction equation
[CH2:1]([N:3](CC)CCN)[CH3:2].CO[C:11]([C:13]1[N:14]=[N:15][N:16]([C:33]2[CH:38]=[C:37]([CH:39]([CH3:41])[CH3:40])[C:36]([O:42]CC3C=CC=CC=3)=[CH:35][C:34]=2[O:50]CC2C=CC=CC=2)[C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][NH:25][CH2:26][CH2:27][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:20][CH:19]=1)=[O:12].[Br-]>C(#N)C>[CH2:1]([NH:3][C:11]([C:13]1[N:14]=[N:15][N:16]([C:33]2[CH:38]=[C:37]([CH:39]([CH3:41])[CH3:40])[C:36]([OH:42])=[CH:35][C:34]=2[OH:50])[C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][NH:25][CH2:26][CH2:27][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:20][CH:19]=1)=[O:12])[CH3:2]

Participants

4

Reactant 2

HCID 259Bromide ionHCID 67985175HCID 67985175, compound

Product 1

HCID 57407244HCID 57407244, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-5-{4-[(2-diethylamino-ethylamino)-methyl]-phenyl}-1H-[1,2,3]triazole-4-carboxylic acid methyl ester N,N-diethylethylenediamine (0.6 mmol) was added at −10° C. to an acetonitrile solution of the bromide adduct obtained in Step A (125 mg, 0.2 mmol), and the reaction mixture was stirred for 30 minutes at this temperature and then warmed up to RT. After completion of the reaction (monitored by TLC), the solvent was removed under reduced pressure and the residue was purified by flash chromatography, the column being previously conditioned with ammonia (DCM/MeOH:80/10). The title compound was obtained as an oil (45%).

Workup

  1. customAfter completion of the reaction (monitored by TLC)
  2. customthe solvent was removed under reduced pressure
  3. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-efeca25074474fbf91a7f4b923841004
Source dataset
uspto-grants-2016_04
Patent number
US09302998B2

Reaction notes

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