Trifluoroacetic acid methylene chloride → HCID 178513159, compound

HRID 1783429Notes

Reaction equation

HRID 1783429 reaction equation
COC1C=CC(C[C@@:8]2([C:26]([O-:28])=[O:27])[C@@H:11]([CH2:12][CH:13]=[N:14][NH:15][C:16]([NH2:18])=[NH:17])[C:10](=[O:19])[N:9]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=CC=1.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[NH:15]([N:14]=[CH:13][CH2:12][C@H:11]1[C:10](=[O:19])[N:9]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[C@@H:8]1[C:26]([OH:28])=[O:27])[C:16]([NH2:18])=[NH:17]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 178489863HCID 178489863, compound

Product 1

HCID 178513159HCID 178513159, compound

Procedure

The crude ester 82 was treated with TFA/DCM (0.75 mL/1 mL). After one and half hours, LC-MS analysis indicated completion of the reaction. The solvent was removed and the residue was purified by preparative HPLC (Vydac reverse phase C-18 column, 22×250 mm ID). Mobil phase: A=0.1% TFA in water, B=0.1% TFA in acetonitrile. The flow rate was 12 mL/min. The gradient time was 5% B to 50% B over 45 min. The desired product, 83, was obtained as a white solid (5.5 mg). Anal. C19H24N6O4, Mol. Wt.: 290.28. Found: ESI-MS: 291.0 (M+H)+.

Workup

  1. customcompletion of the reaction
  2. customThe solvent was removed
  3. customthe residue was purified by preparative HPLC (Vydac reverse phase C-18 column, 22×250 mm ID)
  4. customover 45 min

Sources & evidence

ORD record
ord-7572a4c322e0451fab264ba5f3042b63
Source dataset
uspto-grants-2009_03
Patent number
US07501404B2

Reaction notes

Loading…