HCID 11757073, compound → HCID 10343214, compound

HRID 2211677Notes

Reaction equation

HRID 2211677 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([CH2:12][O:13][C:14]2[CH:19]=[C:18]([NH:20][C:21]([C:23]3[C:24]([NH:29][CH2:30][C:31]4[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=4)=[N:25][CH:26]=[CH:27][CH:28]=3)=[O:22])[CH:17]=[CH:16][C:15]=2[Cl:38])[CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH:8]1[CH2:11][CH:10]([CH2:12][O:13][C:14]2[CH:19]=[C:18]([NH:20][C:21](=[O:22])[C:23]3[CH:28]=[CH:27][CH:26]=[N:25][C:24]=3[NH:29][CH2:30][C:31]3[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=3)[CH:17]=[CH:16][C:15]=2[Cl:38])[CH2:9]1

Participants

3

Reactant 1

HCID 11757073HCID 11757073, compound

Product 1

HCID 10343214HCID 10343214, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

To a solution of 10 mL of TFA/CH2Cl2 (1:1) was added 3-(2-chloro-5-{[2-(4-fluoro-benzylamino)-pyridine-3-carbonyl]-amino}-phenoxymethyl)-azetidine-1-carboxylic acid tert-butyl ester (270 mg, 0.5 mmol) at 0° C. The solution was stirred for 2 h at RT. The solvents were removed in vacuo. The residue was diluted in 30 mL of EtOAc and washed with 30 mL of saturated aqueous NaHCO3, then brine. The resulting organic phase was dried over MgSO4 and concentrated in vacuo. The title compound was purified by column chromatography (silica gel, 5% 2N NH3 in MeOH/EtOAc) and isolated as a white solid. MS (ES+): 442 (M+H)+. Calc'd for C23H22ClFN4O2-440.90.

Workup

  1. customThe solvents were removed in vacuo
  2. additionThe residue was diluted in 30 mL of EtOAc
  3. washwashed with 30 mL of saturated aqueous NaHCO3
  4. dry with materialThe resulting organic phase was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe title compound was purified by column chromatography (silica gel, 5% 2N NH3 in MeOH/EtOAc)
  7. customisolated as a white solid

Sources & evidence

ORD record
ord-4d04e32e0abc4158a06645cca62b7c70
Source dataset
uspto-grants-2006_09
Patent number
US07101868B2

Reaction notes

Loading…