Ethylamine → HCID 178464889, compound

HRID 2388999Notes

Reaction equation

HRID 2388999 reaction equation
F[P-](F)(F)(F)(F)F.[N:8]1(OC(N(C)C)=[N+](C)C)[C:12]2N=CC=C[C:11]=2N=N1.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33]1[C:41]2[C:36](=[N:37][CH:38]=[C:39]([C:42]3[CH:43]=[C:44]([C:51]([N:53]([CH3:55])[CH3:54])=[O:52])[CH:45]=[C:46]([CH:50]=3)[C:47](O)=[O:48])[CH:40]=2)[N:35](COCC[Si](C)(C)C)[N:34]=1.C(N)C.C(N(C(C)C)CC)(C)C>O1CCCC1>[CH2:12]([NH:8][C:47](=[O:48])[C:46]1[CH:50]=[C:42]([C:39]2[CH:40]=[C:41]3[C:33]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=4[O:26][CH3:25])=[N:34][NH:35][C:36]3=[N:37][CH:38]=2)[CH:43]=[C:44]([C:51]([N:53]([CH3:55])[CH3:54])=[O:52])[CH:45]=1)[CH3:11]

Participants

6

Reactant 4

HCID 6341EthylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57975835HCID 57975835, compound

Product 1

HCID 178464889HCID 178464889, compoundYield 13.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a microwave vial O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexa-fluorophosphate (34.8 mg, 0.9 mmol) was added to a solution of 5-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-N,N-dimethyl-iso-phthalamic acid (50 mg, 0.09 mmol), ethyl amine (69 μL, 0.14 mmol), and di-iso-propyl ethyl amine (47.8 μL, 0.27 mmol) in tetrahydrofuran (1 mL). The vial was sealed and the solution irradiated to 100° C. for 10 min in a microwave reactor. The solvent was then removed on under reduced pressure. Trifluoroacetic acid (1 mL) was then added to the residue and the mixture stirred at room temperature for 16 hours. The solvent was then removed under reduced pressure and the residue purified by preparative high pressure liquid chromatography to give N-ethyl-5-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-N′,N′-dimethyl-isophthalamide (5.30 mg, 13% yield). 1H-NMR (500 MHz, Dimethyl sulfoxide-d6) δ 1.15 (t, J=14 Hz, 3H) 2.97 (s, 3H); 3.03 (s, 3H)); 3.29 (dq, J=5.5 Hz, J=7 Hz, 2H); 3.84 (s, 3H); 7.11 (t, J=7.5 Hz 1H); 7.23 (d, J=8 Hz 1H) 7.48 (t, J=7.5 Hz, 1H); 7.67 (d, J=8 Hz 1H); 7.86 (s, 1H); 7.94 (s, 1H); 8.25 (s, 1H); 8.45 (s, 1H); 8.69 (t, J=5.5 Hz, 1H); 8.94 (s, 1H); 13.88 (s, br, 1H) MS: m/z 444.0 (M+H+).

Workup

  1. customThe vial was sealed
  2. customthe solution irradiated to 100° C. for 10 min in a microwave reactor
  3. customThe solvent was then removed on under reduced pressure
  4. additionTrifluoroacetic acid (1 mL) was then added to the residue
  5. customThe solvent was then removed under reduced pressure
  6. customthe residue purified by preparative high pressure liquid chromatography

Sources & evidence

ORD record
ord-a79e5a3557c44ae6b5b7513ca8547a82
Source dataset
uspto-grants-2012_09
Patent number
US08268994B2

Reaction notes

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