2-Thiophenecarboxylic acid → HCID 68561280, compound

HRID 2375483Notes

Reaction equation

HRID 2375483 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[CH3:42][O:43][C:44]1[CH:45]=[C:46]([NH:50][C:51]2[CH:56]=[C:55]([N:57]([CH3:59])[CH3:58])[N:54]=[C:53]([N:60]3[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]3)[N:52]=2)[CH:47]=[CH:48][CH:49]=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:42][O:43][C:44]1[CH:45]=[C:46]([NH:50][C:51]2[CH:56]=[C:55]([N:57]([CH3:59])[CH3:58])[N:54]=[C:53]([N:60]3[CH2:65][CH2:64][N:63]([C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)=[O:8])[CH2:62][CH2:61]3)[N:52]=2)[CH:47]=[CH:48][CH:49]=1

Participants

7

Reactant 5

HCID 107002-Thiophenecarboxylic acidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68563369HCID 68563369, compound

Product 1

HCID 68561280HCID 68561280, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-thiophenecarboxylic acid (15 mg, 0.12 mmol), DIPEA (129 mg, 1.00 mmol) and O-(7-azabenzotriazol-1-yl)N,N,N′,N′-tetramethyluronium hexafluorophosphate (44 mg, 0.12 mmol) in DMF (5 mL) was stirred at room temperature for 30 minutes. N4-(3-methoxyphenyl)-N6,N6-dimethyl-2-(1-piperazinyl)-4,6-pyrimidinediamine (36 mg, 0.10 mmol) was added to the above mixture and stirred at room temperature for 16 h. The crude product was treated with saturated NaHCO3 (50 mL) and extracted with EtOAC (3×50 mL). The organic layer washed with brine (2×100 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by chromatography on silica using hexane/EtOAc (1:3), giving the desired product (25 mg, 57%).

Workup

  1. stirringstirred at room temperature for 16 h
  2. extractionextracted with EtOAC (3×50 mL)
  3. washThe organic layer washed with brine (2×100 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by chromatography on silica

Sources & evidence

ORD record
ord-d1d56af23e2a4cbdb6b46f724462b56d
Source dataset
uspto-grants-2008_12
Patent number
US07465750B2

Reaction notes

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