Potassium Carbonate → 2-{4-[1-(2-Fluoro-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidin-1-yl}-1-(4-trifluoromethoxy-phenyl)-ethanone

HRID 1864114Notes

Reaction equation

HRID 1864114 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:12]1[C:16]2=[N:17][CH:18]=[N:19][C:20]([O:21][CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[C:15]2[CH:14]=[N:13]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:35][C:36]([C:38]1[CH:43]=[CH:42][C:41]([O:44][C:45]([F:48])([F:47])[F:46])=[CH:40][CH:39]=1)=[O:37]>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:9])=[O:10])[CH:5]=[CH:4][C:3]=1[N:12]1[C:16]2=[N:17][CH:18]=[N:19][C:20]([O:21][CH:22]3[CH2:23][CH2:24][N:25]([CH2:35][C:36]([C:38]4[CH:39]=[CH:40][C:41]([O:44][C:45]([F:46])([F:47])[F:48])=[CH:42][CH:43]=4)=[O:37])[CH2:26][CH2:27]3)=[C:15]2[CH:14]=[N:13]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27786912-Bromo-1-[4-(trifluoromethoxy)phenyl]ethan-1-oneHCID 218975531-(2-fluoro-4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 218975032-{4-[1-(2-Fluoro-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidin-1-yl}-1-(4-trifluoromethoxy-phenyl)-ethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 10 mL round-bottomed flask fitted with a N2 inlet was placed a stir bar, 1-(2-fluoro-4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine (43 mg, 0.1 mmol), K2CO3. (138 mg, 1 mmol) and DMF (1 mL). 2-Bromo-1-(4-trifluoromethoxy-phenyl)-ethanone (30 mg, 0.1 mmol) was added in one portion. The reaction mixture was stirred at room temperature for 30 minutes. The resulting suspension was filtered and concentrated under vacuum. The crude was purified by preparative HPLC to give Compound A94. 1H NMR (CDCl3, 400MHz) δ 2.43 (m, 2H), 2.59 (m, 2H), 3.14 (s, 3H), 3.68 (m, 2H), 3.78 (m, 2H), 4.78 (s, 2H), 5.81 (m, 1H), 7.35 (d, 2H), 7.96 (m, 3H), 8.01 (m, 2H), 8.42 (s, 1H), 8.65 (s, 1H). Exact mass calculated for C26H23F4N5O5S 593.14, found 594.3 (MH+).

Workup

  1. customIn a 10 mL round-bottomed flask fitted with a N2 inlet
  2. filtrationThe resulting suspension was filtered
  3. concentrationconcentrated under vacuum
  4. customThe crude was purified by preparative HPLC
  5. customto give Compound A94

Sources & evidence

ORD record
ord-b2663d012d4c4d8da1b1160d5d19f92a
Source dataset
uspto-grants-2009_12
Patent number
US07625906B2

Reaction notes

Loading…