Trifluoroacetic acid → HCID 22291467, compound

HRID 457304Notes

Reaction equation

HRID 457304 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([N:10]3[C:18]4[C:17]5[CH:19]=[C:20]([NH:23][C:24]([C:26]6[C:27]([NH:32]CC7C=CC(OC)=CC=7)=[N:28][CH:29]=[CH:30][CH:31]=6)=[O:25])[CH:21]=[CH:22][C:16]=5[CH2:15][CH2:14][C:13]=4[C:12]([C:42]([NH2:44])=[O:43])=[N:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[NH2:32][C:27]1[C:26]([C:24]([NH:23][C:20]2[CH:21]=[CH:22][C:16]3[CH2:15][CH2:14][C:13]4[C:12]([C:42]([NH2:44])=[O:43])=[N:11][N:10]([C:8]5[CH:7]=[CH:6][C:5]6[O:1][CH2:2][O:3][C:4]=6[CH:9]=5)[C:18]=4[C:17]=3[CH:19]=2)=[O:25])=[CH:31][CH:30]=[CH:29][N:28]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 22291608HCID 22291608, compound

Product 1

HCID 22291467HCID 22291467, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The title compound of Example 209 (1.96 g, 0.0033 mol) was dissolved in 6 mL CH2Cl2 and reacted with 5 mL TFA at room temperature for 36 h. The crude reaction mixture was diluted with CH2Cl2 and basified with a saturated aqueous solution of Na2CO3. The layers were separated and the organic layer was dried over MgSO4. The residue obtained after removal of the solvent under vacuum was triturated with EtOH to afford 0.503 g of title compound (yield: 32%). Mp: 265–267° C. 1H NMR (300 MHz, d6-DMSO): δ 2.88–2.95 (m, 4H), 6.12 (s, 2H), 5.58–6.62 (dd, 1H, J=7.6 Hz, 4.7 Hz), 6.97–7.08 (m, 4H), 7.17 (d, 1H, J=1.9 Hz), 7.28 (s, 1H), 7.32 (s, 2H), 7.55 (s, 2H), 7.95–7.98 (dd, 1H, J=7.7 Hz, 1.7 Hz), 8.11–8.13 (dd, 1H, J=4.7 Hz, 1.7 Hz), 9.99 (s, 1H). M+1=469.

Workup

  1. customThe crude reaction mixture
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over MgSO4
  4. customThe residue obtained
  5. customafter removal of the solvent under vacuum
  6. customwas triturated with EtOH

Sources & evidence

ORD record
ord-eb5220a150334f82ac79053e109ee52c
Source dataset
uspto-grants-2007_03
Patent number
US07186743B2

Reaction notes

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