O-Phenylenediamine → HCID 78322991, compound

HRID 2276712Notes

Reaction equation

HRID 2276712 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:18])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O)[CH:5]=[N:6][CH:7]=1.CN(C(O[N:27]1N=[N:34][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.NC1C=CC=CC=1N>CN(C=O)C.O>[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[NH:34][C:15](=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]([NH:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1)=[O:18]

Participants

7

Reactant 4

HCID 7243O-PhenylenediamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 90388860HCID 90388860, compound

Product 1

HCID 78322991HCID 78322991, compoundYield 55.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of 7-((5-bromopyridin-3-yl)amino)-7-oxoheptanoic acid (1.0 g, 3.2 mmol) in DMF (30 mL) was added HBTU (1.8 g, 4.7 mmol), DIEA (0.82 g, 6.3 mmol), 1,2-diaminobenzene (1.04 g, 9.6 mmol). The solution was stirred at 35° C. for 2 h. After TLC showed the reaction was completed, 50 mL water was added to the solution. The mixture was stirred at room temperature, for 30 min. Then the mixture was filtered to give the crude product as a yellow solid. The crude product was recrystallized by methanol to give product as a yellow solid (yield 55.9%).

Workup

  1. stirringThe mixture was stirred at room temperature, for 30 min
  2. filtrationThen the mixture was filtered
  3. customto give the crude product as a yellow solid
  4. customThe crude product was recrystallized by methanol

Sources & evidence

ORD record
ord-66abef9daa424bd59dbb37052ccbacda
Source dataset
uspto-grants-2015_09
Patent number
US09133105B2

Reaction notes

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