2-Methylbenzoic acid → HCID 59324121, compound

HRID 551447Notes

Reaction equation

HRID 551447 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[CH2:44]([NH:46][CH2:47][C:48]([CH2:54][NH:55][C:56]1[CH:64]=[C:63]([CH3:65])[CH:62]=[C:61]2[C:57]=1[CH:58]=[N:59][N:60]2[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)([OH:53])[C:49]([F:52])([F:51])[F:50])[CH3:45]>CN(C)C=O>[CH2:44]([N:46]([CH2:47][C:48]([OH:53])([CH2:54][NH:55][C:56]1[CH:64]=[C:63]([CH3:65])[CH:62]=[C:61]2[C:57]=1[CH:58]=[N:59][N:60]2[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)[C:49]([F:52])([F:51])[F:50])[C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[CH3:1])[CH3:45]

Participants

6

Reactant 4

HCID 83732-Methylbenzoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 593241363-(Ethylamino)-1,1,1-trifluoro-2-{[(6-methyl-1-phenyl-1H-indazol-4-yl)amino]methyl}-2-propanol

Product 1

HCID 59324121HCID 59324121, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a solution of 2-methylbenzoic acid (12.7 mg, 0.09 mmol) in N,N-dimethylformamide (100 μl) was added a solution of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (34 mg, 0.09 mmol) in dimethylformamide (150 μl) followed by N,N-diisopropylethylamine (36 μl, 0.21 mmol). The mixture was shaken for 5 minutes and then a solution of 3-(ethylamino)-1,1,1-trifluoro-2-{[(6-methyl-1-phenyl-1H-indazol-4-yl)amino]methyl}-2-propanol (27 mg, 0.07 mmol) in N,N-dimethylformamide (150 μl) was added. The mixture was again shaken for 5 minutes and then left to stand at room temperature for 18 hours. The crude reaction was purified by mass-directed autopreparation (System A) to give the title compound (21.1 mg).

Workup

  1. stirringThe mixture was again shaken for 5 minutes
  2. waitleft
  3. waitto stand at room temperature for 18 hours
  4. customThe crude reaction
  5. customwas purified by mass-directed autopreparation (System A)

Sources & evidence

ORD record
ord-ae5c8d82fc9b4cf4b899459ea0080f8a
Source dataset
uspto-grants-2011_05
Patent number
US07947727B2

Reaction notes

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