Dimethylamine → HCID 178489385, compound

HRID 886584Notes

Reaction equation

HRID 886584 reaction equation
F[P-](F)(F)(F)(F)F.N1([O:17]C(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.O[C:26]1[CH:27]=[CH:28][C:29]([CH2:58][C:59](O)=[O:60])=[N:30][C:31]=1[C:32]1[CH:33]=[C:34]2[C:40]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[O:47][CH3:48])=[N:39][N:38](CCOCC[Si](C)(C)C)[C:35]2=[N:36][CH:37]=1.[CH3:62][NH:63][CH3:64].C(N(C(C)C)CC)(C)C>O1CCCC1>[OH:17][CH:58]([C:29]1[CH:28]=[CH:27][CH:26]=[C:31]([C:32]2[CH:33]=[C:34]3[C:40]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=4[O:47][CH3:48])=[N:39][NH:38][C:35]3=[N:36][CH:37]=2)[N:30]=1)[C:59]([N:63]([CH3:64])[CH3:62])=[O:60]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69299634HCID 69299634, compound

Product 1

HCID 178489385HCID 178489385, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a microwave vial O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (53.9 mg, 0.14 mmol) was added to a solution of 5-hydroxy-{6-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxylethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-pyridin-2-yl}-acetic acid (71 mg, 0.14 mmol), dimethyl amine (2 M in THF, 65 μl, 0.14 mmol) and di-iso-propyl ethyl amine (75 μl, 0.43 mmol) in tetrahydrofuran (1 ml). The vial was sealed and the solution irradiated to 70° C. for 10 min in a microwave reactor. The solvent was then removed under reduced pressure and 1 ml of trifluoroacetic acid was added this reaction was stirred for 16 hours and the solvent evaporated under reduced pressure, and purified by preparative mass-triggered reverse-phase HPLC to afford 2-hydroxy-2-{6-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-pyridin-2-yl}-N,N-dimethyl-acetamide (13.6 mg, 24% yield). 1H NMR (500 MHz, Dimethyl sulfoxide-d6) δ 2.85 (s, 3H) 3.30 (s, 3H); 3.85 (s, 3H)); 5.63 (m, 2H); 7.10 (t, J=8 Hz 1H); 7.4 (d, J=8 Hz 1H); 7.44 (m, 2H); 7.63 (d, J=8 Hz 1H); 7.87 (m, 2H) 8.88 (s, 1H); 9.22 (s, 1H); 13.84 (s, br, 1H) MS: m/z 404.3 (M+H+).

Workup

  1. customThe vial was sealed
  2. customthe solution irradiated to 70° C. for 10 min in a microwave reactor
  3. customThe solvent was then removed under reduced pressure and 1 ml of trifluoroacetic acid
  4. additionwas added this reaction
  5. customthe solvent evaporated under reduced pressure
  6. custompurified by preparative mass-triggered reverse-phase HPLC

Sources & evidence

ORD record
ord-59ecf298c67447b99a5d9427fa1b9f49
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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