Ethanol → HCID 86679637, compound

HRID 577694Notes

Reaction equation

HRID 577694 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]2[N:9]=[C:10]([O:31][C:32]3[CH:33]=[C:34]([NH:38][C:39](=[O:42])[CH:40]=[CH2:41])[CH:35]=[CH:36][CH:37]=3)[C:11]3[C:16]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)=[CH:15][N:14](COCC[Si](C)(C)C)[C:12]=3[N:13]=2)[CH:4]=[N:3]1.C(O)(C(F)(F)F)=O.C(O)C.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.O>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]2[N:9]=[C:10]([O:31][C:32]3[CH:33]=[C:34]([NH:38][C:39](=[O:42])[CH:40]=[CH2:41])[CH:35]=[CH:36][CH:37]=3)[C:11]3[C:16]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)=[CH:15][NH:14][C:12]=3[N:13]=2)[CH:4]=[N:3]1

Participants

7

Reactant 4

HCID 702EthanolHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 86679638HCID 86679638, compound

Product 1

HCID 86679637HCID 86679637, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-{3-[(2-[(1-methyl-1H-pyrazol-4-yl)amino]-5-(pyridin-3-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy]phenyl}prop-2-enamide (123 mg, 0.21 mmol) in DCM (10 mL) was added TFA (0.6 mL). The reaction solution was stirred at rt for 3 hrs. The volatiles were removed to give a residue. To the residue was added ethanol (20 mL), water (2 mL), and K2CO3 (142 mg) and the reaction mixture was stirred at rt for 1 hr. The volatiles were removed and water (10 mL) was added. The resulting solid was collected by filtration, washed with water (10 mL) and dried to give the title product (92.8 mg, 100% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.80 (br. s., 1H) 10.32 (br. s., 1H) 8.99-9.14 (m, 1H) 8.95 (d, J=1.51 Hz, 1H) 8.41 (dd, J=4.78, 1.51 Hz, 1H) 8.12 (d, J=7.55 Hz, 1H) 7.64 (br. s., 2H) 7.47 (s, 2H) 7.39 (dd, J=7.93, 4.91 Hz, 1H) 7.21 (br. s., 1H) 7.04 (br. s., 1H) 6.34-6.48 (m, 1H) 6.19-6.31 (m, 1H) 5.70-5.82 (m, 1H) 3.58 (br. s., 3H). m/z (APCI+) for C24H20N8O2 453.0 (M+H)+.

Workup

  1. customThe volatiles were removed
  2. customto give a residue
  3. stirringthe reaction mixture was stirred at rt for 1 hr
  4. customThe volatiles were removed
  5. additionwater (10 mL) was added
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with water (10 mL)
  8. customdried

Sources & evidence

ORD record
ord-075acf9584d5469f8557bf67c241a1e4
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

Loading…