Formic Acid → HCID 53329715, compound

HRID 1029028Notes

Reaction equation

HRID 1029028 reaction equation
[NH2:1][C:2]1[C:11]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:18]3[C:23]([CH2:24][CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=[CH:20][C:19]=3[C:30]([N:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)=[O:31])[CH:8]=2)[N:3]=1.C(O)=[O:38]>C(Cl)Cl>[NH2:1][C:2]1[C:11]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:18]3[C:19]([C:30]([N:32]4[CH2:33][CH2:34][CH2:35][CH2:36]4)=[O:31])=[CH:20][CH:21]=[CH:22][C:23]=3[C:24](=[O:38])[CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 67325503HCID 67325503, compound

Product 1

HCID 53329715HCID 53329715, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2-(2-amino-3-morpholinoquinolin-6-yl)-3-(3,3-dimethylbut-1-ynyl)phenyl)(pyrrolidin-1-yl)methanone (188 mg, 0.390 mmol, see Example 45) in formic acid (>96%) (10 mL, 265 mmol) was heated to 110° C. After 4 days CH2Cl2 was added and the solution was washed with water and sodium carbonate solution. The organic phase was separated and dried over MgSO4. The solvent was removed under reduced pressure and the remaining residue was purified by preparative HPLC (10-100% water with 0.1% TFA/CH3CN, 11 min). The obtained product was eluted on an SCX cartridge with MeOH followed by 2M NH3/MeOH. The basic fraction was concentrated to afford the titled compound as a white powder. MS (ESI, pos. ion) m/z: 501 (M+1).

Workup

  1. washthe solution was washed with water and sodium carbonate solution
  2. customThe organic phase was separated
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customthe remaining residue was purified by preparative HPLC (10-100% water with 0.1% TFA/CH3CN, 11 min)
  6. washThe obtained product was eluted on an SCX cartridge with MeOH
  7. concentrationThe basic fraction was concentrated

Sources & evidence

ORD record
ord-9fea1ba515464a578f2fe36754a4839a
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

Loading…