Trifluoroacetic acid → HCID 117728020, compound

HRID 1772741Notes

Reaction equation

HRID 1772741 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:8]3[N:9]([CH:32]=[C:33]([CH2:35][O:36][C:37]4[CH:46]=[CH:45][C:44]5[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=5)[N:38]=4)[N:34]=3)[C:10]([C:13]3[CH:14]=[CH:15][C:16]([N:19]4[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]4)=[N:17][CH:18]=3)=[CH:11][N:12]=2)=[CH:3][CH:2]=1.[C:47]([OH:53])([C:49]([F:52])([F:51])[F:50])=[O:48]>C(Cl)Cl>[F:50][C:49]([F:52])([F:51])[C:47]([OH:53])=[O:48].[N:19]1([C:16]2[N:17]=[CH:18][C:13]([C:10]3[N:9]4[CH:32]=[C:33]([CH2:35][O:36][C:37]5[CH:46]=[CH:45][C:44]6[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=6)[N:38]=5)[N:34]=[C:8]4[C:7]([C:4]4[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=4)=[N:12][CH:11]=3)=[CH:14][CH:15]=2)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117732310HCID 117732310, compound

Product 1

HCID 117728020HCID 117728020, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of compound 87e (60.0 mg, 0.0976 mmol) in 3 mL of DCM at rt was added TFA (0.50 mL). The resulting mixture was stirred at rt for 1 h. The solvent was removed under reduced pressure and the residue was triturated with Et2O. The solid was collected by filtration and washed with Et2O. After drying under reduced pressure, the title compound 120 was obtained as an orange solid. 1H-NMR (CD3OD; 400 MHz) 9.36 (d, J=6.1 Hz, 2H), 8.92 (d, J=6.1 Hz, 2H), 8.62 (s, 1H), 8.30 (s, 1H), 8.05-8.20 (m, 3H), 7.82 (t, J=7.3 Hz, 2H), 7.66 (t, J=7.8 Hz, 1H), 7.43 (t, J=7.3 Hz, 1H), 7.14 (d, J=8.8 Hz, 1H), 7.01 (d, J=8.8 Hz, 1H), 5.82 (s, 2H), 3.96-4.04 (m, 4H), 3.34-3.41 (m, 4H). Mass spectrum (LCMS, ESI pos.): Calcd. for C30H26N8O, 515.2 (M+H). found 515.2.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was triturated with Et2O
  3. filtrationThe solid was collected by filtration
  4. washwashed with Et2O
  5. customAfter drying under reduced pressure

Sources & evidence

ORD record
ord-e55aaa1cc23d4ad6b24a210ea916010a
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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