Trifluoroacetic acid → HCID 178510051, compound

HRID 1987059Notes

Reaction equation

HRID 1987059 reaction equation
C(O)(C(F)(F)F)=O.C1(OC)C=CC=CC=1.C(OC([N:23]=[C:24]([N:26](C(OC(C)(C)C)=O)[O:27][CH2:28][CH2:29][NH:30][C:31](=[O:54])[CH2:32][C:33]1[C:38]([C:39]#[N:40])=[CH:37][CH:36]=[C:35]([NH:41][CH2:42][C:43]([F:52])([F:51])[C:44]2[CH:49]=[CH:48][CH:47]=[C:46]([Cl:50])[CH:45]=2)[C:34]=1[F:53])[NH2:25])=O)(C)(C)C>C(Cl)Cl>[C:24]([NH:26][O:27][CH2:28][CH2:29][NH:30][C:31](=[O:54])[CH2:32][C:33]1[C:38]([C:39]#[N:40])=[CH:37][CH:36]=[C:35]([NH:41][CH2:42][C:43]([C:44]2[CH:49]=[CH:48][CH:47]=[C:46]([Cl:50])[CH:45]=2)([F:51])[F:52])[C:34]=1[F:53])(=[NH:23])[NH2:25]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 86595385HCID 86595385, compound

Product 1

HCID 178510051HCID 178510051, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of TFA (7.5 mL, 97 mmol) and anisole (3.0 mL, 27.6 mmol) in DCM (23 mL) was added to N-[2-(N′,N″-bis(tert-butoxycarbonyl)amidinoaminooxy)ethyl]-2-{3-[(2,2-difluoro-2-(3-chlorophenyl)ethyl)amino]-6-cyano-2-fluorophenyl}acetamide (2.18 g, 3.26 mmol), as prepared in the preceding step, at room temperature. The dark yellow solution was stirred for 10 h, and then concentrated. The residue was subjected to flash chromatography (DCM/MeOH saturated with gaseous NH3; 95:5→90:10) to yield 1.286 g (84%) of the title compound as a white solid. 1H NMR (300 MHz, CD3OD) δ 7.57-7.55 (m, 1H), 7.51-7.40 (m, 3H), 7.27 (dd, J=8.6 Hz, 1.3 Hz, 1H), 6.77 (t, J=8.4 Hz, 1H), 3.93 (t, J=13.6 Hz, 2H), 3.80 (t, J=5.4 Hz, 2H), 3.74 (d, J=2.0 Hz, 2H), 3.43 (t, J=5.4 Hz, 2H). LC/MS (ESI) calcd for C20H21ClF3N6O2 (MH+) 469.1. found 469.2.

Workup

  1. customas prepared in the preceding step, at room temperature
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-0b6be5b1e3c242d7b129a10ed739974d
Source dataset
uspto-grants-2009_06
Patent number
US07550474B2

Reaction notes

Loading…