Triethylamine → {4-[1-(4-Methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidin-1-yl}-pyridin-3-yl-methanone

HRID 719452Notes

Reaction equation

HRID 719452 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]3=[N:16][CH:17]=[N:18][C:19]([O:20][CH:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)=[C:14]3[CH:13]=[N:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(N(CC)CC)C.Cl.[C:35](Cl)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[N:38][CH:37]=1>CN(C=O)C>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]3=[N:16][CH:17]=[N:18][C:19]([O:20][CH:21]4[CH2:26][CH2:25][N:24]([C:35]([C:36]5[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=5)=[O:42])[CH2:23][CH2:22]4)=[C:14]3[CH:13]=[N:12]2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 113608021-(4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 11442982{4-[1-(4-Methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidin-1-yl}-pyridin-3-yl-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a 500 mL round-bottomed flask was placed Compound A6 (146 mg, 0.36 mmol) and triethylamine (300 μl). DMF (15 mL) was added to completely dissolve the solid material. Nicotinoyl chloride hydrochloride (96 mg, 0.54 mmol) was added to the solution and the mixture was stirred overnight under N2 at room temperature. After all of the starting amine was completely converted as indicated by LCMS, the reaction was stopped by quenching with water. The reaction mixture was then concentrated under vacuum and purified by preparative HPLC to give Compound A7. 1H NMR (CDCl3, 400 MHz) δ 2.06 (m, 2H), 2.22 (m, 2H), 3.09 (s, 3H), 3.55 (m, 1H), 3.79 (m, 2H), 4.15 (m, 1H), 5.76 (m, 1H), 7.86 (m, 1H), 8.11 (d, 2H), 8.28 (s, 1H), 8.33 (d, 1H), 8.61 (d, 2H), 8.68 (s, 1H), 8.84 (m, 1H), 8.92 (m, 1H). LCMS calculated for C23H22N6O4S 478.14, observed 479.1 (MH+)

Workup

  1. customInto a 500 mL round-bottomed flask was placed
  2. dissolutionto completely dissolve the solid material
  3. customby quenching with water
  4. concentrationThe reaction mixture was then concentrated under vacuum
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-9844644a0ac4477893d52567b310d978
Source dataset
uspto-grants-2006_11
Patent number
US07132426B2

Reaction notes

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