HCID 57699527, compound → HCID 57699517, compound

HRID 883802Notes

Reaction equation

HRID 883802 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([N:17]([CH3:39])[C:18]3[CH:19]=[CH:20][C:21]([CH2:24][N:25]4[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[C@@H:27]([CH3:38])[CH2:26]4)=[N:22][CH:23]=3)=[O:16])[CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:3]=[C:4]([NH:8][CH:9]2[CH2:10][CH2:11][N:12]([C:15]([N:17]([CH3:39])[C:18]3[CH:23]=[N:22][C:21]([CH2:24][N:25]4[CH2:30][CH2:29][NH:28][C@@H:27]([CH3:38])[CH2:26]4)=[CH:20][CH:19]=3)=[O:16])[CH2:13][CH2:14]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 57699527HCID 57699527, compound

Product 1

HCID 57699517HCID 57699517, compoundYield 91.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1,1-dimethylethyl (2S)-4-({5-[({4-[(3-fluorophenyl)amino]-1-piperidinyl}carbonyl)(methyl)amino]-2-pyridinyl}methyl)-2-methyl-1-piperazinecarboxylate (D62) (320 mg, 0.593 mmol) in DCM (16 ml) and TFA (4 ml) was stirred at room temp for 2 h. The solvent was removed in vacuo and the residue was taken up in MeOH, and loaded onto an (solute SCX cartridge which was eluted with MeOH then 2M NH3 in MeOH. The ammoniacal fraction was concentrated to give the crude product as a yellow oil. Column chromatography eluting with 0-10% (2M NH3 in MeOH)/DCM gave the title compound as a pale yellow oil (240 mg). MS (ES) MH+ 441.3.

Workup

  1. customThe solvent was removed in vacuo
  2. washwas eluted with MeOH
  3. concentrationThe ammoniacal fraction was concentrated
  4. customto give the crude product as a yellow oil
  5. washColumn chromatography eluting with 0-10% (2M NH3 in MeOH)/DCM

Sources & evidence

ORD record
ord-4ba73776a67944309d165f8df7c8896b
Source dataset
uspto-grants-2012_08
Patent number
US08236953B2

Reaction notes

Loading…