2-Thiophenecarboxylic acid → HCID 68561280, compound

HRID 1352899Notes

Reaction equation

HRID 1352899 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 was 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 was 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-75630fb86f7445298e9ffe82654577d5
Source dataset
uspto-grants-2007_05
Patent number
US07220775B2

Reaction notes

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