Benzoic Acid → HCID 178447119, compound

HRID 2235472Notes

Reaction equation

HRID 2235472 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:41][C:42]1[NH:43][C:44]2[C:45]([N:63]=1)=[CH:46][C:47]1[C:48]([CH3:62])([CH3:61])[C:49](=[O:60])[N:50]([CH2:53][C:54](=[O:59])[C:55]([CH3:58])([CH3:57])[CH3:56])[C:51]=1[CH:52]=2>CN(C)C=O>[CH3:56][C:55]([CH3:58])([CH3:57])[C:54](=[O:59])[CH2:53][N:50]1[C:51]2[CH:52]=[C:44]3[NH:43][C:42]([NH:41][C:1](=[O:9])[C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[N:63][C:45]3=[CH:46][C:47]=2[C:48]([CH3:61])([CH3:62])[C:49]1=[O:60]

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178447120HCID 178447120, compound

Product 1

HCID 178447119HCID 178447119, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of benzoic acid (85.5 mg), TBTU (225 mg; 0.70 mmol) and DIPEA (240 μl) in N,N-dimethylformamide (8 ml) is stirred at RT for 5 min. Afterwards D7 (210 mg) is added and the mixture is stirred at RT for 18 h. After evaporation of the solvent the crude material is purified by RP-MPLC eluted with MeCN/water to give the desired compound (186 mg).

Workup

  1. customAfter evaporation of the solvent the crude material
  2. customis purified by RP-MPLC
  3. washeluted with MeCN/water

Sources & evidence

ORD record
ord-f1ec42567f694b8cbf0fa138b0524c4b
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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