Trifluoroacetic acid → Trifluoroacetic acid

HRID 607251Notes

Reaction equation

HRID 607251 reaction equation
C([O:8][C:9]1[CH:45]=[CH:44][C:12]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[NH:24][C:23]4[CH:25]=[C:26]([Br:29])[CH:27]=[CH:28][C:22]=4[N:21]=3)=[CH:16][C:15]=2[NH:30][C:31]2[C:32]3[CH:40]=[CH:39][C:38]([CH:41]([CH3:43])[CH3:42])=[N:37][C:33]=3[N:34]=[CH:35][N:36]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.CC1C(C)=C(C)C(C)=C(C)C=1.[F:57][C:58]([F:63])([F:62])[C:59]([OH:61])=[O:60]>>[Br:29][C:26]1[CH:27]=[CH:28][C:22]2[N:21]=[C:20]([C:17]3[CH:18]=[CH:19][C:14]([O:13][C:12]4[CH:11]=[CH:10][C:9]([OH:8])=[CH:45][CH:44]=4)=[C:15]([NH:30][C:31]4[C:32]5[CH:40]=[CH:39][C:38]([CH:41]([CH3:42])[CH3:43])=[N:37][C:33]=5[N:34]=[CH:35][N:36]=4)[CH:16]=3)[NH:24][C:23]=2[CH:25]=1.[F:57][C:58]([F:63])([F:62])[C:59]([OH:61])=[O:60]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12784PentamethylbenzeneHCID 66808430HCID 66808430, compound

Product 2

HCID 6422Trifluoroacetic acidYield 47%HCID 60204799HCID 60204799, compound

Procedure

A solution of the product from Example 147D (38.8 mg, 0.059 mmol) and pentamethylbenzene (87 mg, 0.5901 mmol) in trifluoroacetic acid (5 mL) was stirred at room temperature for 2 hours. The solvent was removed by rotary evaporation under vacuum and co-evaporated with methylene chloride/hexanes (2×). The resulting solid was triturated with hexanes (3×) and purified by HPLC with TFA to provide the title compound as a trifluoroacetic acid salt (22 mg, 47%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.36 (d, J=6.99 Hz, 6H), 3.20-3.39 (m, 1H), 6.78 (d, J=8.82 Hz, 2H), 6.95 (d, J=9.19 Hz, 2H), 7.02 (d, J=8.82 Hz, 1H), 7.36 (dd, J=8.64, 2.02 Hz, 1H), 7.55 (d, J=8.46 Hz, 1H), 7.78 (d, J=1.47 Hz, 1H), 7.91 (d, J=8.82 Hz, 1H), 8.11 (dd, J=8.64, 2.02 Hz, 1H), 8.35 (d, J=1.84 Hz, 1H), 8.94 (s, 1H), 9.03 (d, J=8.82 Hz, 1H), 9.46 (br s, 1H), 11.63 (br s, 1H); MS (APCI+) m/z 567/569 (M+H)+.

Workup

  1. customThe solvent was removed by rotary evaporation under vacuum and co-evaporated with methylene chloride/hexanes (2×)
  2. customThe resulting solid was triturated with hexanes (3×)
  3. custompurified by HPLC with TFA

Sources & evidence

ORD record
ord-4cb8959d22fb41be937fe2bb25e45686
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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