Ethylene Glycol → HCID 24986280, compound

HRID 2251081Notes

Reaction equation

HRID 2251081 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[N:25]([C:26]2[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:27]=2[F:33])[C:13]2[N:14]=[C:15]([NH:18][C@@H:19]([CH3:24])[C:20]([OH:23])([CH3:22])[CH3:21])[N:16]=[CH:17][C:12]=2[CH:11]=1)=[O:9].[CH2:34]([OH:37])[CH2:35]O.[F-:38].[F-].[F-].B>C(Cl)Cl.O>[F:33][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]([F:32])[C:26]=1[N:25]1[C:13]2[N:14]=[C:15]([NH:18][CH:19]([CH3:24])[C:20]([CH3:22])([OH:23])[CH3:21])[N:16]=[CH:17][C:12]=2[CH:11]=[C:10]1[C:8]1([C:3]2[CH:2]=[CH:7][C:6]([F:38])=[CH:5][CH:4]=2)[O:37][CH2:34][CH2:35][O:9]1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 24990692HCID 24990692, compoundHCID 178419221HCID 178419221, compound2×

Product 1

HCID 24986280HCID 24986280, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-(2-chlorophenyl)-[7-(2,6-difluorophenyl)-2-(2-hydroxy-1,2-dimethyl-propylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-methanone, 8, (0.17 g, 0.36 mmol) and ethylene glycol (0.045 ml, 0.726 mmol) in CH2Cl2 (2 ml) is added borane trifluoride etherate (0.02 ml, 0.15 mmol) and the mixture is stirred for 17 hours at room temperature. Additional borane trifluoride etherate (0.01 ml) is added as needed to drive the reaction to completion. The reaction mixture is diluted with H2O and extracted with EtOAc the combined organic phases are washed with additional H2O, aqueous NH4Cl solution, dried (MgSO4), filtered and concentrated in vacuo. The residue is purified over silica (50% EtOAc/hexanes, then 80% EtOAc/hexanes) to afford 68 mg of the desired product as a yellow solid: 1H NMR (300 MHz, CDCl3) δ 8.48 (s, 1H), 7.43-6.92 (m, 7H), 6.47 (s, 1H), 8.0 Hz, 1H), 3.98-3.84 (m, 6H), 1.22-1.15 (m, 9H); HRMS calcd for C26H25F3N4O3 (M+H)+ 499.1957, found 499.1946.

Workup

  1. customthe reaction to completion
  2. extractionextracted with EtOAc the combined organic phases
  3. washare washed with additional H2O, aqueous NH4Cl solution
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified over silica (50% EtOAc/hexanes

Sources & evidence

ORD record
ord-b6c6330a79884c53a7ab46f6e0f36504
Source dataset
uspto-grants-2008_01
Patent number
US07319102B1

Reaction notes

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